Catalytic Asymmetric Nitroso‐Diels–Alder Reaction with Acyclic Dienes | Zendy

Yamamoto Yuhei | Zendy; Yamamoto Hisashi | Zendy

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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.

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