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Inside Cover: Design of Peptidyl Thiourea Derivatives as Organocatalysts for the Asymmetric Ring Opening of meso ‐Stilbene Oxides (Asian J. Org. Chem. 6/2014)
Author(s) -
Chimni Swapandeep Singh,
Kumar Vikas,
Bala Neeraj
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201490011
Subject(s) - chemistry , organocatalysis , thiourea , nucleophile , enantioselective synthesis , epoxide , ring (chemistry) , tripeptide , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , amino acid , biochemistry
Organocatalysis Organocatalytic asymmetric ring opening of epoxides with aliphatic amines has always been a challenge. In their Communication on page 700 ff., Swapandeep Singh Chimni report the design and synthesis of chiral peptidyl thiourea organocatalysts for the asymmetric ring opening of epoxides with N ‐phenylpiperazines. A tripeptide scaffold with a β‐turn nucleating element provides favorable stereochemistry by positioning the nucleophile close to the epoxide. Chiral β‐amino alcohols were obtained with up to 95% ee after crystallization. The configuration at the N‐terminal residue of the catalyst affects the stereochemical outcome of the reaction.