Asymmetric Synthesis of  cis ‐3,4‐Disubstituted Chromans and Dihydrocoumarins  via  an Organocatalytic Michael Addition/ Hemiacetalization Reaction | Zendy

Enders Dieter | Zendy; Wang Chuan | Zendy; Yang Xuena | Zendy; Raabe Gerhard | Zendy

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Asymmetric Synthesis of cis ‐3,4‐Disubstituted Chromans and Dihydrocoumarins via an Organocatalytic Michael Addition/ Hemiacetalization Reaction

Author(s) -

Enders Dieter,

Wang Chuan,

Yang Xuena,

Raabe Gerhard

Publication year - 2010

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.201000659

Subject(s) - chemistry , domino , catalysis , michael reaction , organocatalysis , cascade reaction , organic chemistry , epimer , medicinal chemistry , enantioselective synthesis

The organocatalytic domino Michael/hemiacetalization reaction between various aldehydes and ortho ‐nitrovinylphenols has been developed. Under the catalysis of diphenyl prolinol trimethylsilyl ether, cis ‐3,4‐disubstituted chromanols are obtained in high to excellent yields (81–98%) and stereoselectivities ( dr : 86:14 to >99:1, ee 96 to >99%). The corresponding disubstituted chromans are available by dehydroxylation of the domino products in good to excellent yields (58–95%). Furthermore, oxidation of the domino products with pyridinium chlorochromate provided 3,4‐dihydrocoumarins in good yields (65–83%) without any epimerization.

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