The Journal of organic chemistry

Formation of Chiral C (sp3)− C (sp) Bond by Allylic Substitution of Secondary Allylic Picolinates and Alkynyl Copper Reagents

Y Kiyotsuka, Y Kobayashi

Index: Kiyotsuka, Yohei; Kobayashi, Yuichi Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7489 - 7495

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Citation Number: 20

Abstract

To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine) CO2-,(2-pyrazine) CO2-,(EtO) 2PO2-, C6F5CO2-, o-(Ph2P) C6H4CO2-, MeOCO2-, or AcO-group were examined. First, picolinate (R1= Me, R2= CH2OPMB) was subjected to reaction with (TMS-C C) 2CuLi· LiBr at 0° C. Although no substitution took place, MgBr2 (3 equiv) was found to promote the reaction to ...