Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions

TETRAHEDRON LETTERS

卷:52

Article

Yang, Dexi¹  Belardi, Justin K.²  Micalizio, Glenn C.¹ 

[1] Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA

[2] Yale Univ, Dept Chem, New Haven, CT 06520 USA

关键词: Stereoselective synthesis;    Reductive cross-coupling;    Allylic alcohol;    Titanium alkoxide;    Quaternary center;   

DOI  :  10.1016/j.tetlet.2010.11.059

来源: Elsevier

【 摘 要 】

Regioselective titanium alkoxide-mediated reductive cross-coupling reactions of allylic alcohols with vinylsilanes and imines have previously been demonstrated to proceed with allylic transposition by formal metallo-[3,3]-rearrangement [thought to proceed by a sequence of: (1) directed carbometalation, and (2) syn-elimination]. While many examples have been described that support this reaction path, a collection of substrates have recently been identified that react by way of an alternative pathway, delivering a concise convergent route to coupled products bearing a quaternary center. (C) 2010 Elsevier Ltd. All rights reserved.

【 授权许可】

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