Year: 1994
Type: article
Abstract: Nonracemic a-and γ-alkoxy and silyloxy allylic stannanes are easily prepared through reduction of acyl stannanes with chiral hydrides such as BINAL-H or Chirald followed by etherification of the hydroxy stannane products.The α-isomers add to aldehydes to afford mainly syn adducts which can be converted to γ-lactones upon hydrolysis and oxidation.This reaction can be used to prepare cyclic adducts which serve as useful intermediates for the synthesis of cembrane natural products.With achiral aldehydes, matched/mismatched pairing is observed.The stereochemical outcome is consistent with an acyclic Felkin-Ahn transition state.γ-Alkoxy stannanes show analogous reactivity.Additions to aldehydes lead to syn 1,2-diol derivatives.Matched/mismatched pairings are observed with α-chiral aldehydes.The reaction is particularly useful as a method for carbohydrate chain extension.
Source: Main Group Metal Chemistry
Author: James A. Marshall,
Institution: University of South Carolina
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $1,187
OpenAlex ID: W2949363713