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A New Strategy for Extending N ‐Acyl Imides as Chiral Auxiliaries for Aldol and Diels–Alder Reactions: Application to an Enantioselective Synthesis of α‐Himachalene

1997; Wiley; Volume: 36; Issue: 19 Linguagem: Inglês

10.1002/anie.199721191

ISSN

1521-3773

Autores

David A. Evans, David H. Brown Ripin, Jeffrey S. Johnson, Eileen A. Shaughnessy,

Tópico(s)

Analytical Chemistry and Chromatography

Resumo

Angewandte Chemie International Edition in EnglishVolume 36, Issue 19 p. 2119-2121 CommunicationFull Access A New Strategy for Extending N-Acyl Imides as Chiral Auxiliaries for Aldol and Diels–Alder Reactions: Application to an Enantioselective Synthesis of α-Himachalene† Prof. David A. Evans, Corresponding Author Prof. David A. Evans Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this authorDavid H. Brown Ripin, David H. Brown Ripin Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this authorJeffrey S. Johnson, Jeffrey S. Johnson Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this authorEileen A. Shaughnessy, Eileen A. Shaughnessy Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this author Prof. David A. Evans, Corresponding Author Prof. David A. Evans Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this authorDavid H. Brown Ripin, David H. Brown Ripin Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this authorJeffrey S. Johnson, Jeffrey S. Johnson Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this authorEileen A. Shaughnessy, Eileen A. Shaughnessy Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code +(617)495-1460, e-mail: [email protected]Search for more papers by this author First published: October 17, 1997 https://doi.org/10.1002/anie.199721191Citations: 33 † Financial support was provided by the U. S. National Science Foundation and the National Institutes of Health. AboutPDF 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 New application for a chiral auxilary: N-acyl imides like 1, which is formed in an enantioselective aldol reaction, can be converted into thioesters and decarboxylated to give 2 (TES = Et3Si). The oxazolidinone auxiliary is thus removed under mild conditions in a one-pot reaction, which is a key step in the elegant synthesis of the title compound. References 1 S. Shambayati, S. L. Schreiber in Comprehensive Organic Synthesis, Vol. 1 (Eds; B. M. Trost, I. Fleming). Pergamon, New York, 1991, pp. 283–324. 2(a) D. Enders, B. B. Lohray, Angew. Chem. 1988, 100 594–596; Angew. Chem. Int. Ed. Engl. 1988, 27, 581–582; (b) B. B. Lohary, D. Enders, Helv. Chim. Acta 1989, 72 980–984; (c) B. B. Lohary, R. Zimbiniski, Tetrahedron Lett. 1990, 31, 7273–7276. 3(a) Another important approach to the construction of ketone-derived chiral auxiliaries has been through the use of chiral metalloenamines: S. F. Martin in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, pp. 475–502. 4(a) C. H. Heathcock, M. C. Pirrung, C. T. Buse, J. P. Hagen, S. D. Young, J. E. Shon, J. Am. Chem. Soc. 1979, 101, 7077–7079; (b) S. Masamune, W. Choy, F. A. Kerdesky, B. Imperiali, J. Am. Chem. Soc. 1981, 103, 1566–1568; (c) S. Masamune, L. A. Reed III, J. T. Davis, W. Choy, J. Org. Chem. 1983, 48, 1154–1156. 5 D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154–1156. 6 The experimental details for the synthesis of 1, have been reported: D. A. Evans, H. P. Ng, J. S. Clark, D. L. Rieger, Tetrahedron 1992, 48 2127–2142. 7 D. A. Evans, J. S. Clark, R. Metternich, V. J. Novack, G. S. Sheppard, J. Am. Chem. Soc. 1990, 112 866–868. 8 D. A. Evans, F. Urpi, T. C. Somers, J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112 8215–8216. 9(a) D. A. Evans, H. P. Ng, D. L. Riger, J. Am. Chem. Soc. 1995, 115, 11446–11459 (see the transformation 7→18 in Scheme VIII); (b) D. A. Evans, A. M. Ratz, B. E. Huff, G. S. Sheppard, J. Am. Chem. Soc. 1995, 117, 3448–3467 (see the transformation 4→17 in scheme VII). 10(a) Initial studies utilizing the Krapcho decarboxylation conditions (DMSO, H2O, 140°C) on β-oxoimide aldol adducts afforded only moderate yields of the desired ketone products accompanied by significant amounts of β-elimination: A. P. Krapcho, Synthesis 1982, 805–822, (b) 893–914. 11 R. E. Damon, G. M. Coppola, Tetrahedron Lett. 1990, 31 2849–2852. 12(a) E. J. Corey, M. C. Bock, Tetrahedron Lett. 1975, 3269–3270; (b) R. Schwyzer, C. Hurlimann, Helv. Chim. Acta 1954, 18, 155–166. 13 Thiophenolate and 2-methyl-2-propanethiolate both failed to react, while benzylthiolate provides results comparable to those of ethanethiolate. 14(a) J. L. Duffy, T. P. Yoon, D. A. Evans, Tetrahedron Lett. 1995, 36, 9245–9248; (b) D. A. Evans, M. G. Yang, M. J. Dart, J. L. Duffy, Tetrahedron Lett. 1996, 37, 1957–1960; (c) D. A. Evans, M. G. Yang, M. J. Dart, J. L. Duffy, A. S. Kim. J. Am. Chem. Urpi, J. Am. Chem. Soc. 1995, 117, 9598–9599; (d) D. A. Evans, D. L. Rieger, M. T. Bilodeau, F. Urpi, J. Am. Chem. Soc. 1991, 113, 1047–1049; (e) D. A. Evans, M. J. Dart, J. L. Duffy, D. L. Rieger, J. Am. Chem. Soc. 1995, 117, 9073–9074. 15(a) T. C. Joseph, S. Dev, Tetrahedron Lett. 1961, 216–222; (b) Tetrahedron 1968, 24, 3841–3852, 3853–3859; (c) W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592–2597; (d) E. Wenkert, K. Naemura, Synth. Comm. 1973 3, 45–48. 16 D. A. Evans, J. Bartroli, T. L. Shih. J. Am. Chem. Soc. 1981, 103, 2127–2129. 17 J. R. Parikh, W. von E. Doering, J. Am. Chem. Soc. 1967, 89, 5505–5507. 18 S. H. Pine, R. Zahler, D. A. Evans, R. H. Grubbs. J. Am. Chem. Soc. 1980, 102, 3270–3272. Citing Literature Volume36, Issue19October 17, 1997Pages 2119-2121 ReferencesRelatedInformation

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