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  • Highly catalytic asymmetric addition of deactivated alkyl grignard reagents to aldehydes.

Highly catalytic asymmetric addition of deactivated alkyl grignard reagents to aldehydes.

Organic letters (2009-11-17)
Chao-Shan Da, Jun-Rui Wang, Xiao-Gang Yin, Xin-Yuan Fan, Yi Liu, Sheng-Li Yu
ABSTRACT

Generally used and highly reactive RMgBr reagents were effectively deactivated by bis[2-(N,N-dimethylamino)ethyl] ether and then were employed in the highly enantioselective addition of Grignard reagents to aldehydes. The reaction was catalyzed by the complex of commercially available (S)-BINOL and Ti(O(i-)Pr)(4) under mild conditions. Compared with the other observed Grignard reagents, alkyl Grignard reagents showed higher enantioselectivity and they achieved >99% ee.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Bis[2-(N,N-dimethylamino)ethyl] ether, 97%