INOETHYL)APOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE - AN IMPROVED CHIRAL REDUCING AGENT FOR STRAIGHT-CHAIN ALIPHATIC-KETONES

Authors
WEISSMAN SA RAMACHANDRAN PV
Citation
Sa. Weissman et Pv. Ramachandran, INOETHYL)APOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE - AN IMPROVED CHIRAL REDUCING AGENT FOR STRAIGHT-CHAIN ALIPHATIC-KETONES, Tetrahedron letters, 37(22), 1996, pp. 3791-3794
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
22
Year of publication
1996
Pages
3791 - 3794
Database
ISI
SICI code
0040-4039(1996)37:22<3791:IH-AI>2.0.ZU;2-V
Abstract
A series of chirally modified borohydrides of the type lithium 2-(alky l)apopinocampheyl-9-borabicyclo[3.3.1]nonyl hydride (2-4 and 8-9) were prepared to enable a strategic development of chiral reagents for the reduction of straight chain aliphatic ketones. Reagent 8 (alkyl = 2-d iethylaminoethyl) reduces 2-octanone in 82% ee, significantly higher t han that obtained with NB-Enantride (7) under identical conditions. An improved methodology for these reductions is also described. Copyrigh t (C) 1996 Elsevier Science Ltd