ChemInform Abstract: Tandem Diastereo‐ and Enantioselective Preparation of Aryl and Alkyl Cyclopropyl Carbinols with Three Adjacent Stereocenters Using Perhydrobenzoxazines and Diethylzinc.

Abstract

and Diethylzinc. -The asymmetric ethylation of aldehydes (I) and a subsequent cyclopropanation with in situ generated F 3C-CH2-O-Zn-CH2-I lead to ethyl cyclopropyl carbinols (IV) with high diastereoselectivity and good enantioselectivity. The analogous sequence using in situ generated Et-Zn-Ph reagent for the asymmetric phenylation step gives rise to phenyl cyclopropyl carbinols (VIII) and (IX). -(INFANTE, R.; NIETO*, J.; ANDRES, C.; Org. Biomol. Chem. 12 (2014) 2, 345-354, http://dx.doi.org/10.1039/c3ob41797b ; Dep. Quim. Org., Fac. Cienc., Univ. Valladolid, E-47011 Valladolid, Spain; Eng.) -R. Staver 23-104