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Organocatalytic Asymmetric Michael Addition of Oxazolones to Arylsulfonyl Indoles: Facile Access to syn ‐Configured α,β‐Disubstituted Tryptophan Derivatives
Author(s) -
Cai ChangWu,
Zhu XingLi,
Wu Song,
Zuo ZongLe,
Yu LiangLiang,
Qin DaBin,
Liu QuanZhong,
Jing LinHai
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201335
Subject(s) - stereocenter , chemistry , michael reaction , enantioselective synthesis , tryptophan , adduct , organocatalysis , imine , optically active , combinatorial chemistry , organic chemistry , stereochemistry , amino acid , catalysis , biochemistry
Enantioselective Michael addition of oxazolones to in situ generated vinylogous imine intermediates is reported. A series of optically active 3‐alkylindole derivatives with adjacent quaternary and tertiary stereocenters was obtained. The resulting adducts can readily be converted into syn ‐configured α,β‐disubstituted tryptophan derivatives without compromising the stereoselectivities.