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The Enantioselective, Organocatalyzed Diels–Alder Reaction of 2‐Vinylindoles with α,β‐Unsaturated Aldehydes: An Efficient Route to Functionalized Tetrahydrocarbazoles
Author(s) -
Zheng Changwu,
Lu Yingpeng,
Zhang Junkang,
Chen Xingkuan,
Chai Zhuo,
Ma Wenying,
Zhao Gang
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000130
Subject(s) - enantioselective synthesis , diels–alder reaction , catalysis , chemistry , organocatalysis , computer science , combinatorial chemistry , organic chemistry
Prolinol catalysts : A highly enantio‐ and diastereoselective prolinol‐catalyzed Diels–Alder reaction of 2‐vinylindoles and α,β‐unsaturated aldehydes is developed (see scheme). This methodology allows the development of further applications of prolinols in asymmetric synthesis. The resulting densely functionalized enantiomerically pure tetrahydrocarbazoles are useful in the total synthesis of natural products such as the core structure of the akuammiline alkaloid vincorine.