Premium
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.