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Asymmetric Formal [3+2] Cycloaddition Reaction of Succinaldehyde and Nitroalkene Catalyzed by Diphenylprolinol Silyl Ether
Author(s) -
Umemiya Shigenobu,
Hayashi Yujiro
Publication year - 2015
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.201500623
Subject(s) - nitroalkene , chemistry , enantioselective synthesis , domino , silylation , cycloaddition , silyl ether , pyridine , catalysis , organocatalysis , organic chemistry , michael reaction , ether
The enantioselective domino Michael/Henry reaction of nitroalkenes with succinaldehyde was found to proceed efficiently upon using diphenylprolinol silyl ether as the organocatalyst. The reaction affords cis ‐disubstituted nitropentenes with excellent diastereoselectivities and enantioselectivities after treatment of the Michael product with Ac 2 O and pyridine.