Molecular Recognition of α,β-Unsaturated Carbonyl Compounds Using Aluminum Tris(2,6-diphenylphenoxide) (ATPH): Structural and Conformational Analysis of ATPH Complexes and Application to the Selective Vinylogous Aldol Reaction
2003; American Chemical Society; Volume: 125; Issue: 20 Linguagem: Inglês
10.1021/ja0205941
ISSN1943-2984
AutoresSusumu Saito, Takashi Nagahara, Masahito Shiozawa, Masakazu Nakadai, Hisashi Yamamoto,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoVarious alpha,beta-unsaturated carbonyl compounds were coordinated with aluminum tris(2,6-diphenylphenoxide) (ATPH) to give the corresponding Lewis acid-base complexes in a distinctive coordination fashion (selective coordination). ATPH recognizes carbonyl substrates and subsequently orients itself as it forms a stable complex through selective coordination with the carbonyl oxygen. Selective coordination also confers a conformational preference to each carbonyl compound under the steric and electronic influence of ATPH, which enables the vinylogous aldol reaction of alpha,beta-unsaturated carbonyl compounds to give the corresponding gamma-aldol products with different regio- and stereoselectivities.
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