Pericyclic Cascade with Chirality Transfer: Reaction Pathway and Origin of Enantioselectivity of the Hetero‐Claisen Approach to Oxindoles | Zendy

ÇelebiÖlçüm Nihan | Zendy; Lam Yuhong | Zendy; Richmond Edward | Zendy; Ling Kenneth B. | Zendy; Smith Andrew D. | Zendy; Houk Kendall N. | Zendy

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Pericyclic Cascade with Chirality Transfer: Reaction Pathway and Origin of Enantioselectivity of the Hetero‐Claisen Approach to Oxindoles

Author(s) -

ÇelebiÖlçüm Nihan,

Lam Yuhong,

Richmond Edward,

Ling Kenneth B.,

Smith Andrew D.,

Houk Kendall N.

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201105412

Subject(s) - pericyclic reaction , chirality (physics) , sigmatropic reaction , stereoselectivity , cycloaddition , chemistry , stereochemistry , claisen rearrangement , cascade , combinatorial chemistry , organic chemistry , physics , particle physics , catalysis , quantum chromodynamics , chromatography , nambu–jona lasinio model , chiral symmetry breaking

A new pericyclic cascade is proposed for the chiral auxiliary‐controlled synthesis of 3,3‐disubstituted oxindoles from nitrones and ketenes. The remarkable acyclic 1,6‐stereochemical induction, hitherto unexplained, is rationalized by a stereoselective 3+2 cycloaddition step, which installs the stereochemistry, and a chirality transfer step facilitated by a hetero‐[3,3]‐sigmatropic rearrangement (see picture; PG=protecting group).

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