Premium
Regio‐ and Diastereoselective Crotylboration of vic ‐Tricarbonyl Compounds
Author(s) -
Roßbach Jan,
Baumeister Julia,
Harms Klaus,
Koert Ulrich
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201517
Subject(s) - chemistry , diastereomer , regioselectivity , stereochemistry , lewis acids and bases , organic chemistry , catalysis
Crotylboration of vic ‐diketoamides and vic ‐diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas ( E )‐crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer ( anti ), Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.