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Title: Stereoselective [4+2]‐Cycloaddition with Chiral Alkenylboranes
Abstract

A method for the stereoselective [4+2]‐cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N‐protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C−B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.

 
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NSF-PAR ID:
10149514
Author(s) / Creator(s):
 ;  ;  ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Angewandte Chemie
Volume:
132
Issue:
28
ISSN:
0044-8249
Page Range / eLocation ID:
p. 11529-11536
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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