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Synfacts 2006(7): 0658-0658  
DOI: 10.1055/s-2006-941846
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclic β-Amino Acids by RCM

Contributor(s): Victor Snieckus, Todd Macklin
G. Lesma, B. Danieli, A. Saccheti, A. Silvani*
Università degli Studi di Milano, Italy
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

Reported is an elegant method for the synthesis of chiral, cyclic β-amino acid derivatives initiating from the common precursor 1, prepared by a reductive amination/desymmetrization sequence of commercial dimethyl 2-oxoglutarate in high yield (>96% ee ) on multigram scale (M. Ohno et al. J. Am. Chem. Soc. 1981, 103, 2405-2406). The final RCM products contain an endocyclic double bond for potential further chemical functionalization.