Highly selective reduction of acyclic beta-alkoxy ketones to protected syn-1,3-diols.
[reaction: see text] The conversion of 1-(2-methoxyethoxy)ethyl-protected beta-hydroxy ketones to syn-1,3-ethylidene acetals is effected by Et(3)SiH and SnCl(4). This reaction is proposed to proceed via a cyclic oxocarbenium ion intermediate and provides the products in yields that range from 69 to 94% and with diastereoselectivities that are >200:1.
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Aaron J
AJ
Cullen
Tarek
T
Sammakia
D000438:Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D007659:Ketones