0

Asymmetric Alkyldifluoroboranes and Their Use in Secondary Amine Synthesis

Donald S Matteson, Gyung Youn Kim

Org Lett. 2002 Jun 27;4(13):2153-5.

PMID: 12074655

Abstract:

[reaction: see text] Asymmetric diol boronic esters with potassium bifluoride form the corresponding alkyltrifluoroborate and free diol under mild conditions. Defluoridation with tetrachlorosilane produces an alkyldifluoroborane intermediate. This conversion of relatively unreactive boronic esters to derivatives that are strong Lewis acids opens new synthetic opportunities, as illustrated by the preparation of (R)-2-phenylpyrrolidine in 98% ee from a pinanediol or 1,2-dicyclohexyl-1,2-ethanediol boronic ester via potassium (2-phenyl-4-azidobutyl)trifluoroborate.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
LS7931465 Potassium [4-(diethylamine-1-carbonyl)phenyl]trifluoroborate Potassium [4-(diethylamine-1-carbonyl)phenyl]trifluoroborate Price
qrcode