Highly Enantioselective Conjugate Addition–Cyclization Cascade Reaction of Malonates with  o ‐Hydroxycinnamaldehydes: Asymmetric Synthesis of 4‐Substituted Chromanols | Zendy

Lee Yongcheon | Zendy; Seo Seung Woo | Zendy; Kim SungGon | Zendy

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Highly Enantioselective Conjugate Addition–Cyclization Cascade Reaction of Malonates with o ‐Hydroxycinnamaldehydes: Asymmetric Synthesis of 4‐Substituted Chromanols

Author(s) -

Lee Yongcheon,

Seo Seung Woo,

Kim SungGon

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.201100324

Subject(s) - chemistry , enantioselective synthesis , conjugate , organocatalysis , cascade reaction , combinatorial chemistry , cascade , organic chemistry , catalysis , stereochemistry , mathematical analysis , mathematics , chromatography

The asymmetric organocatalytic conjugate addition–cyclization reaction of malonates with o ‐hydroxycinnamaldehydes, which affords 4‐substituted chroman‐2‐ols, has been established using a diphenylprolinol trimethylsilyl (TMS) ether as organocatalyst. The desired products were obtained with good to excellent yields and high enantioselectivities (up to >99% ee ). Synthetically useful chroman derivatives were formed after subsequent reactions.

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