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Stereodivergent Addition of 4‐Silyloxy‐1,2‐Allenes to Aldehydes by Hydroboration

2010; Wiley; Volume: 16; Issue: 38 Linguagem: Inglês

10.1002/chem.201001563

1521-3765

Carolina Sánchez, Xavier Ariza, Josep Cornellà, Jaume Farràs, Jordi García, Jordi Ortiz,

Organoboron and organosilicon chemistry

Chemistry – A European JournalVolume 16, Issue 38 p. 11535-11538 Communication Stereodivergent Addition of 4-Silyloxy-1,2-Allenes to Aldehydes by Hydroboration Carolina Sánchez, Carolina Sánchez Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Xavier Ariza, Dr. Xavier Ariza [email protected] Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorJosep Cornellà, Josep Cornellà Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Jaume Farràs, Dr. Jaume Farràs Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Jordi Garcia, Dr. Jordi Garcia [email protected] Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Jordi Ortiz, Dr. Jordi Ortiz Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this author Carolina Sánchez, Carolina Sánchez Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Xavier Ariza, Dr. Xavier Ariza [email protected] Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorJosep Cornellà, Josep Cornellà Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Jaume Farràs, Dr. Jaume Farràs Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Jordi Garcia, Dr. Jordi Garcia [email protected] Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this authorDr. Jordi Ortiz, Dr. Jordi Ortiz Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona (Spain), Fax: (+34) 933397878Search for more papers by this author First published: 30 August 2010 https://doi.org/10.1002/chem.201001563Citations: 17Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract All-ene one! Three out of four stereoisomers of 2-vinyl-1,3-diols can be obtained from a single allene. A simple variation of the reaction conditions modifies the stereochemical outcome of the addition of an allene to an aldehyde via hydroboration. Stereocontrol is dependent upon the order in which the reagents are mixed (leading to E or Z boron species) and the type of aldehyde (aliphatic or aromatic) used. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_201001563_sm_miscellaneous_information.pdf16.7 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aY. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207–2293; 1bD. Hoppe in Stereoselective Synthesis Methods of Organic Chemistry (Houben–Weyl), E21b, Vol. 3 (Eds.: ), Thieme, Stuttgart, 1996, pp. 1357–1486; 1cW. R. Roush in Stereoselective Synthesis Methods of Organic Chemistry (Houben–Weyl), E21b, Vol. 3 (Eds.: ), Thieme, Stuttgart, 1996, pp. 1410–1486; 1dM. V. Perkins in Science of Synthesis, Vol. 36 (Ed.: ), Thieme, Stuttgart, 2008, pp. 667–753; 1eY. Bubnov in Science of Synthesis, Vol. 36 (Ed.: ), Thieme, Stuttgart, 2008, pp. 945–1064. 2 2aH. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092–2093; 2bP. K. Jadhav, K. S. Bhat, P. T. Perumal, H. C. Brown, J. Org. Chem. 1986, 51, 432–439; 2cH. C. Brown, K. S. Bhat, R. S. Randad, J. Org. Chem. 1989, 54, 1570–1576; 2dP. V. Ramachandran, Aldrichimica Acta 2002, 35, 23–35. 3 3aW. R. Roush, A. E. Walts, L. K. Hoong, J. Am. Chem. Soc. 1985, 107, 8186–8190; 3bW. R. Roush, R. L. Halterman, J. Am. Chem. Soc. 1986, 108, 294–296; 3cW. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz, R. L Halterman, J. Am. Chem. Soc. 1990, 112, 6339–6348. 4R. W. Hoffmann, Pure Appl. Chem. 1988, 60, 123–130. 5For a review on allene chemistry, see: 5a Modern Allene Chemistry (Eds.: ), Wiley-VCH, Weinheim, 2004; 5bS. Ma, Aldrichimica Acta 2007, 40, 91–102; 5cH. H. A. M. Hassan, Curr. Org. Synth. 2007, 4, 413–439; 5dH. Kim, L. J. Williams, Curr. Opin. Drug Discovery Dev. 2008, 11, 870–894. 6 6aH. C. Brown, G. Narla, J. Org. Chem. 1995, 60, 4686–4687; 6bG. Narla, H. C. Brown, Tetrahedron Lett. 1997, 38, 219–222. For some recent examples of the use of functionalized alkenyl boranes prepared by hydroboration, see: 6cY. Yamamoto, R. Fujikawa, A. Yamada, N. Miyaura, Chem. Lett. 1999, 1069–1070; 6dR. Pragani, W. R. Roush, Org. Lett. 2008, 10, 4613–4616; 6eA. Z. González, J. G. Román, E. Alicea, E. Canales, J. A. Soderquist, J. Am. Chem. Soc. 2009, 131, 1269–1273; 6fJ. Kister, A. C. DeBaillie, R. Lira, W. R. Roush, J. Am. Chem. Soc. 2009, 131, 14174–14175; 6gM. Chen, M. Handa, W. R. Roush, J. Am. Chem. Soc. 2009, 131, 14602–14603; 6hF. Li, W. R. Roush, Org. Lett. 2009, 11, 2932–2935; 6iX. Ariza, J. Cornellà, J. Garcia, J. Ortiz, C. Sánchez, M. Font-Bardia, X. Solans, Angew. Chem. 2009, 121, 4266–4269; Angew. Chem. Int. Ed. 2009, 48, 4202–4205. 7 7aY. Georges, Y. Allenbach, X. Ariza, J.-M. Campagne, J. Garcia, J. Org. Chem. 2004, 69, 7387–7390; 7bX. Ariza, J. Garcia, Y. Georges, M. Vicente, Org. Lett. 2006, 8, 4501–4504. 8 8aS. Searles, Y. Li, B. Nassim, M.-T. Robert Lopes, P. T. Tran, P. Crabbé, J. Chem. Soc. Perkin Trans. 1 1984, 747–751; 8bS. Ma, H. Hou, S. Zhao, G. Wang, Synthesis 2002, 1643–1645. 9The enantiomer of syn,syn-3 a was also prepared from allene (R)-1. The enantiomeric purity was >99:1 as determined by HPLC analysis of the corresponding benzoates using a Chiralpak IA column (see the Supporting Information). 10An analogous cyclic transition state for (Z)-2 was assumed to account the formation of anti,anti- and syn,anti-3 a. 11For the relative configurational assignments, see the Supporting Information. 12For a discussion on the configurational stability of allylmetal compounds, see: 12aR. W. Hoffmann, Angew. Chem. 1982, 94, 569–580; Angew. Chem. Int. Ed. Engl. 1982, 21, 555–566. See also: 12bK. K. Wang, Y. G. Gu, C. Liu, J. Am. Chem. Soc. 1990, 112, 4424–4431; 12cD. H. Ess, J. Kister, M. Chen, W. R. Roush, Org. Lett. 2009, 11, 5538–5541. 13Detailed data of the isomeric product composition of crude mixtures are given in the Supporting Information. 14Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004. 15The main minor isomer was syn,syn-3 a. 16The sterically hindered disiamylborane gave also anti,anti-3 a (d.r. 80:9:11 anti,anti/syn,syn/anti,syn) as the major isomer. 17For a successful control of the E/Z configuration by changing the temperature, see: reference [6g]. 18For the stereoselective formation of (Z)-boron intermediates by hydroboration, see: references [6d,f]. 19A. Pelter, K, Smith in Comprehensive Organic Chemistry, Vol. 3 (Eds.: ), Pergamon, Oxford 1979, pp. 689–940. 20Major anti,anti and syn,anti products of Table 3 were easily separated from the mixture of the rest of minor isomers by flash chromatography. The same applies for the syn,syn major compounds in Tables 1 and 2. 21Reference [1b], pp. 1361–1364. 22In contrast with the performed ab initio calculations for the addition of (E)-2-alkenylboranes to aldehydes in which the chair-like transition states are predicted to dominate over boat-like arrangements, the situation is less clear for the (Z)-2-alkenyl boranes where different transition states of similar energy could be found. Citing Literature Volume16, Issue38October 11, 2010Pages 11535-11538 ReferencesRelatedInformation