Tetrahedron

Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols

M Kimura, M Shimizu, S Tanaka, Y Tamaru

Index: Kimura, Masanari; Shimizu, Masamichi; Tanaka, Shuji; Tamaru, Yoshinao Tetrahedron, 2005 , vol. 61, # 15 p. 3709 - 3718

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Citation Number: 40

Abstract

Under catalysis of Pd (OAc) 2-(Pn-Bu) 3, Et2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60–90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio-and stereoselectivities observed for the allylation with unsymmetrically substituted allyl alcohols are discussed.