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Catalytic Asymmetric Nitroso‐Diels–Alder Reaction with Acyclic Dienes
Author(s) -
Yamamoto Yuhei,
Yamamoto Hisashi
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200501345
Subject(s) - trimethylsilyl , adduct , cycloaddition , silylation , chemistry , nitroso , diene , catalysis , nitroso compounds , diels–alder reaction , organic chemistry , medicinal chemistry , natural rubber
Bigger, bulkier, better : Catalytic asymmetric nitroso‐Diels–Alder reactions of nitrosopyridines with silyloxydienes lead to adducts with excellent enantioselectivities (see scheme). The bulk of the silyl group (TMS=trimethylsilyl, TIPS=triisopropylsilyl) forces the diene to adopt an s‐cis configuration in favor of the typical concerted [4+2] cycloaddition. The Diels–Alder adducts can then be converted into protected amino alcohols.