149915-82-2Relevant academic research and scientific papers
High ?-Face Selectivity in Anti Aldol Reactions of E-Enol Borinates from Chiral Alkoxymethyl Ketones: Stereocontrolled Synthesis of a C24-C32 Polyol Subunit of Rapamycin
Paterson, Ian,Tillyer, Richard D.
, p. 4182 - 4184 (2007/10/02)
Using (c-C6H11)2BCl/Et3N, the aldol reactions of the α-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95 percent yield with >/= 95 percent diastereoselectivity.This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of rapamycin (10).
