Chirality transfer from silicon to carbon via diastereoselective Simmons-Smith cyclopropanation of chiral alkenylsilanols

摘要

Simmons-Smith cyclopropanation of a chiral alkenylsilanol with CH2I2 Et2Zn proceeds diastereoselectively to give the corresponding cyclopropylsilanol product. Chirality transfer from silicon to the alkenyl carbons of the silicon substituent is observed. The stereochemistry of the obtained cyclopropylsitanol is confirmed by converting to cyclopropanol via Tamao oxidation. (C) 2002 Elsevier Science Ltd. All rights reserved. [References: 21]