Synthesis and Asymmetric [3 + 2] Cycloaddition Reactions of Chiral Cyclic Nitrone: A Novel System Providing Maximal Facial Bias for both Nitrone and Dipolarophile | Zendy

Ishikawa Teruhiko | Zendy; Tajima Yoshiaki | Zendy; Fukui Miyuki | Zendy; Saito Seiki | Zendy

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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.

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