Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes | Zendy

Lichao Fang | Zendy; Richard P. Hsung | Zendy

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Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes

Author(s) -

Lichao Fang,

Richard P. Hsung

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol500390a

Subject(s) - cycloaddition , chemistry , stereoselectivity , lewis acids and bases , aldimine , selectivity , sulfonyl , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl

A highly stereoselective aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes with N-sulfonyl aldimines is described. While this Lewis acid promoted heterocycloaddition provides an efficient strategy for constructing optically enriched isoquinuclidines, it is mechanistically intriguing. The cycloaddition favored the endo-II pathway in the absence of a viable bidentate coordination. This represents an unexpected switch from the anticipated endo-I selectivity obtained in the all-carbon cycloaddition.

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