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Diastereoselective addition of vinyl organometallic reagents to l-serinal

โœ Scribed by Robert S. Coleman; Andrew J. Carpenter

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
323 KB
Volume
33
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

An examination of the diastereoselective addition of vinyl organometallic reagents to N-BOC L-serinal acetonide (

) to afford mixtures of syn-2 and anti-2 is presented. Vinylzinc chloride in nonpolar solvents was found to add to the aldehyde carbonyl of 1 with h:l synlanti stereoselectivity in excellent yields.

๐Ÿ“œ SIMILAR VOLUMES

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Diastereoselective addition of organometallic reagents to chiral iminium ions: Synthesis of (S)-(+)-cryptostyline I.
โœ Richard P. Polniaszek; Lawrence W. Dillard ๐Ÿ“‚ Article ๐Ÿ“… 1990 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 271 KB

lminium ion 2c participates in stereoselective nucleophilic addition reactions wkh Grfgnard reagents. Analysis of the products from reaction of 5hexenylmagnesium bromide with iminium ion 2a suggests that these reactions proceed by a polar (two electron) mechanism. The utility of this chemistry is de