Generation of Stereochemically Defined Tetrasubstituted Enolborinates by 1,4‐Hydroboration of α,β‐Unsaturated Morpholine Carboxamides with (Diisopinocampheyl)borane | Zendy

Allais Christophe | Zendy; Tsai Andy S. | Zendy; Nuhant Philippe | Zendy; Roush William R. | Zendy

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Generation of Stereochemically Defined Tetrasubstituted Enolborinates by 1,4‐Hydroboration of α,β‐Unsaturated Morpholine Carboxamides with (Diisopinocampheyl)borane

Author(s) -

Allais Christophe,

Tsai Andy S.,

Nuhant Philippe,

Roush William R.

Publication year - 2013

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.201307302

Subject(s) - hydroboration , borane , chemistry , diastereomer , morpholine , amide , aldol reaction , quaternary carbon , stereochemistry , organic chemistry , enantioselective synthesis , catalysis

On all fours : The title reaction with (Ipc) 2 BH provides tetrasubstituted enolborinates which undergo aldol reactions with aldehydes to form products with all‐carbon quaternary centers with exceptional diastereo‐ and enantioselectivity. A change to the substitution pattern of the starting amide leads to either diastereomer of the α‐methyl‐α‐ethyl‐β‐hydroxy carboxamide ( 1 or 2 ).

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