Diastereoselective aldol and reformatsky reactions of alpha-halo carbonyl compounds and aldehydes mediated by titanium(II) chloride

Authors
Kagayama, A Igarashi, K Shiina, I Mukaiyama, T
Citation
A. Kagayama et al., Diastereoselective aldol and reformatsky reactions of alpha-halo carbonyl compounds and aldehydes mediated by titanium(II) chloride, B CHEM S J, 73(11), 2000, pp. 2579-2585
Citations number
39
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
00092673 → ACNP
Volume
73
Issue
11
Year of publication
2000
Pages
2579 - 2585
Database
ISI
SICI code
0009-2673(200011)73:11<2579:DAARRO>2.0.ZU;2-P
Abstract
Highly diastereoselective aldol reactions of alpha -bromo ketones with seve ral aldehydes were successfully carried out by using a combination of titan ium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitri le at low temperature. Similarly, Reformatsky reactions of alpha -bromo thi oester with aliphatic aldehydes proceeded to afford beta -hydroxy thioester s in good yields under mild conditions.