ISSN:
1434-193X
Keywords:
α-Methylene-γ-butyrolactones
;
Indium
;
Amino aldehydes
;
Allyl addition
;
Barbier reaction
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The indium-mediated reaction of Z-protected α-amino aldehydes 1-6 with 2-(bromomethyl)acrylates 8/9 in aqueous solvents has been investigated. The preference for the formation of syn-configured homoallyl alcohols 10-16 (diastereoselectivities ranging from 2:1 to 32:1, yields 68-93%) may be explained by a chelate-controlled reaction. No racemization occurred during the preparation and transformation of the amino aldehydes. Acid-catalyzed esterification (H2SO4 in Et2O) led to α-methylene-γ-butyrolactones 17-22 with yields ranging from 89 to 97%. The configurations of all diastereoisomers were established by five X-ray crystallographic analyses and by comparision of the NMR spectra.Supporting information for this article is available on the WWW under //http://www.wiley-vch.de/contents/jc_2046/1999/98530_s.pdf or from the author.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
Permalink
