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ChemInform Abstract: An Olefination Entry for the Synthesis of Enantiopure α,ω-Diaminodicarboxylates and Azabicyclo[X.Y.0]alkane Amino Acids.

✍ Scribed by Francis Gosselin; William D. Lubell


Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


An Olefination Entry for the Synthesis of Enantiopure α,ω-Diaminodicarboxylates and Azabicyclo[X.Y.0]alkane Amino Acids. -Treatment of aminodicarboxylates of type (I) with methyl phosphonate and subsequent Horner-Wadsworth-Emmons olefination with aldehyde (IV) offers a new and efficient route to diaminodicarboxylates. The latter are useful precursors of azabicycloalkane amino acids. For example, the diaminodicarboxylate (Va) yields, after reductive piperidine ring closure and lactam cyclization, the bicyclic amino acid (IX). -(GOSSELIN, FRANCIS; LUBELL, WILLIAM D.;