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Synlett 2001; 2001(5): 0629-0633
DOI: 10.1055/s-2001-13367
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Solid-Support Synthesis of 1,2-Diols and γ-Lactones Through Addition of α-(Benzoyloxy)crotylindium Reagents to Aldehydes

Janine Cossy* , Chrystelle Rasamison, Domingo Gomez Pardo, James A. Marshall
  • *Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France; Fax 33-1-40-79-46-60; E-mail: janine.cossy@espci.fr
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Publication Date:
31 December 2001 (online)

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A procedure for the solid phase synthesis of 1,2-diols and γ-lactones from α-(hydroxy)crotylstannane has been developed through transmetalation with InBr3. A variety of 1,2-diols and γ-lactones were synthesized in satisfactory yields and, in some cases, with excellent diastereoselectivity. The products are formed free of tin contamination.

solid-phase synthesis - diols - lactones - α-(benzoyloxy)-crotylindium - α-(benzoyloxy)-crotylstannane

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