Asymmetric Synthesis of 2‐Substituted Dihydrobenzofurans and 3‐Hydroxydihydrobenzopyrans through the Enantioselective Epoxidation of  O ‐Silyl‐Protected  ortho ‐Allylphenols | Zendy

Jiang Hang | Zendy; Sugiyama Takaya | Zendy; Hamajima Akinari | Zendy; Hamada Yasumasa | Zendy

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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.

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