165876-49-3Relevant articles and documents
Stereoselective Additions of Chiral, Functionalized Organozinc Reagents to Achiral and Chiral Aldehydes: a Matched-Mismatched Case in Organozinc Chemistry
Koert, Ulrich,Wagner, Holger,Pidun, Ulrich
, p. 1447 - 1458 (2007/10/02)
The additions of the enantiomerically pure organozinc reagents 17 and 33 to the THF-aldehyde 1 in the presence of the monodentate Lewis acid boron trifluoride-ether give the nonchelation-controlled addition products 7 and 36, respectively (stereoselectivity 95:5, 86:14).These results provide a route to oligo(tetrahydrofuran)s with the relative stereochemistry trans-syn-cis.A stereodirecting effect of the chiral center in the organozinc reagent 17 is found, leading to simple diastereoselectivies in the reaction with achiral aldehydes and to a matched-mismatched case in the reaction with the chiral aldehyde 1. - Key Words: Addition, stereoselective, nonchelation-controlled / Reagent, organozinc / Stereodifferentiation, double / Oligo(tetrahydrofuran)