Addition of γ-silyloxyallyltins on ethyl glyoxylate: evaluation of the influence of the experimental conditions on the stereochemical course of the reaction

Ethyl glyoxylate was reacted with α-substituted γ-( t-butyldimethylsilyloxy)-allyltributyltin in order to obtain selectively each diastereomer of ethyl 3-( t-butyldimethylsilyloxy)-2-hydroxyhex-4-enoate and subsequently the corresponding diols. Diastereomers syn- E, anti- E and anti- Z were obtained...

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Bibliographic Details
Published in:Tetrahedron 2010-02, Vol.66 (8), p.1570-1580
Main Authors: Lumbroso, Alexandre, Kwiatkowski, Piotr, Blonska, Anna, Le Grognec, Erwan, Beaudet, Isabelle, Jurczak, Janusz, Jarosz, Slawomir, Quintard, Jean-Paul
Format: Article
Language:English
Subjects:
Allylstannation
Chemical Sciences
Chemistry
Diastereoselective synthesis
Ethyl glyoxylate
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reaction mechanisms
Reactivity and mechanisms
γ-Silyloxyallyltributyltins
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Summary:Ethyl glyoxylate was reacted with α-substituted γ-( t-butyldimethylsilyloxy)-allyltributyltin in order to obtain selectively each diastereomer of ethyl 3-( t-butyldimethylsilyloxy)-2-hydroxyhex-4-enoate and subsequently the corresponding diols. Diastereomers syn- E, anti- E and anti- Z were obtained in good yields with good to high selectivities and the obtained results were rationalized by consideration of cyclic or open transition states in agreement with the experimental conditions and with the structure of the starting reagents. Using appropriate experimental conditions, adducts syn- E, anti- E, anti- Z, were obtained selectively and in good yields. The results were rationalized on the basis of open and cyclic transition states. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.12.037