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Synthesis and Asymmetric [3 + 2] Cycloaddition Reactions of Chiral Cyclic Nitrone: A Novel System Providing Maximal Facial Bias for both Nitrone and Dipolarophile
Author(s) -
Ishikawa Teruhiko,
Tajima Yoshiaki,
Fukui Miyuki,
Saito Seiki
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199618631
Subject(s) - nitrone , cycloaddition , substituent , chemistry , orientation (vector space) , stereochemistry , organic chemistry , mathematics , catalysis , geometry
Only the convex face of the chiral, cyclic nitrone 1 is accessible to dipolarophiles 2 in [3 + 2] cycloadditions. Since in addition Z 2 dictates the orientation of the dipolarophiles by directing the smallest substituent (H) of 2 into the most demanding space, the cycloadducts 3 are obtained with almost perfect stereocontrol.