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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 ).