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Asymmetric Synthesis of 2‐Substituted Dihydrobenzofurans and 3‐Hydroxydihydrobenzopyrans through the Enantioselective Epoxidation of O ‐Silyl‐Protected ortho ‐Allylphenols
Author(s) -
Jiang Hang,
Sugiyama Takaya,
Hamajima Akinari,
Hamada Yasumasa
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000505
Subject(s) - enantioselective synthesis , chemistry , silylation , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
The Shi‐type epoxidation of O ‐ tert‐ butyldiphenylsilyl (TBDPS) protected o ‐allylphenols serves as an efficient strategy to construct the dihydrobenzofurans and dihydrobenzopyrans in up to 97% ee . This methodology led to the enantioselective synthesis of (+)‐marmesin, (−)‐(3′ R )‐decursinol, and (+)‐lomatin.