1.
J Am Chem Soc
; 128(36): 11776-7, 2006 Sep 13.
Article
in English
| MEDLINE
| ID: mdl-16953615
ABSTRACT
A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. By using a mixture of La-Li3-(1a)3 complex (LLB 2a) and La-Li3-(1b)3 (LLB* 2b) complex in a ratio of 2/1, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield.
Subject(s)
Alcohols/isolation & purification , Lanthanum/chemistry , Lithium/chemistry , Nitro Compounds/isolation & purification , Alcohols/chemistry , Hydrogen/chemistry , Ketones/chemistry , Naphthols/chemistry , Nitro Compounds/chemistry , Oxidation-Reduction , Spectrometry, Mass, Electrospray Ionization
2.
Org Lett
; 7(23): 5339-42, 2005 Nov 10.
Article
in English
| MEDLINE
| ID: mdl-16268573
ABSTRACT
[reaction, structure: see text] Chiral Y{N(SiMe3)2}3/linked-BINOL catalyst generated Y-enolate in situ from various hydroxyketones (R2 = aryl, heteroaryl). Beta-amino-alpha-hydroxy ketones (R1 = aryl, heteroaryl, alkenyl) were obtained syn-selectively (up to 96/4) in high ee (up to 98%) and good yield (up to 98% yield).
