Heteroatom Chemistry

Conjugate addition of vinylic organocuprates generated via transmetalation of phenylseleno??substituted vinylzirconates: Functionalization at the 4??position of enones

…, M Suzuki, K Shintaku, H Maeda

Index: Segi, Masahito; Suzuki, Masahiro; Shintaku, Kazuki; Maeda, Hajime Heteroatom Chemistry, 2011 , vol. 22, # 3-4 p. 545 - 552

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Citation Number: 3

Abstract

Abstract Hydrozirconation of propargylic selenides (1) or 4-phenylseleno-1-butyne (2) with Cp 2 ZrHCl, followed by in situ transmetalation to cuprate (Me 2 Cu (CN) Li 2) and addition of enones, led to the formation of 1, 4-adducts in good yields. The adducts derived from 1 were subjected to oxidation with H 2 O 2 to afford allylic alcohol derivatives via [2, 3] sigmatropic rearrangement of allylic selenides. On the other hand, the oxidation of the ...