Synthesis of Homoallylic Chiral Tertiary Alcohols via Chelation-Controlled Diastereoselective Nucleophilic Addition on α-Alkoxyketones: Application for the Synthesis …

PV Ramachandran, H Liu, MV Ram Reddy…

Index: Ramachandran, P. Veeraraghavan; Liu, Haipeng; Reddy, M. Venkat Ram; Brown, Herbert C. Organic Letters, 2003 , vol. 5, # 20 p. 3755 - 3757

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Citation Number: 35

Abstract

Chiral β-syn-alkoxyhomoallylic alcohols derived from alkoxyallylboration of aldehydes upon oxidation provided the corresponding chiral ketones. Chelation-controlled nucleophilic addition to these ketones occurred in a highly stereoselective manner to afford anti- homoallylic tertiary alcohols. This methodology has been applied for the synthesis of the C1- C11 subunit of C8-epi-fostriecin.