Abstract
Homologation of cedranediol boronic esters 1, RBO,C15H,4l with (dichloromethyl)lithium resulted in the formation of (αR)-α-chloro boronic esters 3, RCHCIBO2C15H24, consistently yielding (R)/(S)ratios over 25:1. The absolute configuration of cedranediol (R)-1-chloro-1-phenylmethylboronate 3dR was determined by X-ray diffraction. The distortion of the five-membered 1,3,2-dioxaborolane ring of 3dR from planarity was found. The reason why the cedranediol boronic esters are prone to hydrolysis has been discussed.
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