ISSN:
1434-193X
Keywords:
Pinacol coupling
;
Aldehydes
;
Samarium diiodide
;
1,2-Diols
;
Diastereoselectivity
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-The samarium diiodide pinacol coupling of benzaldehyde and cyclohexanecarboxaldehyde in the presence of a variety of polyethylene glycols, including derivatives containing carbohydrates has been studied. Whereas such complexing agents allow for the formation of 1,2-diols, in the case of benzaldehyde the erythro-isomer predominates with diastereoselectivities of up to 7:1, while with cyclohexanecarboxaldehyde a stereoselectivity of up to 10:1 was observed but in favor of the threo-isomer. This divergence in the stereoselectivity of these two aldehydes suggests the presence of two different mechanisms occurring in these pinacol coupling reactions.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
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