Chiral aminal templates 6. Diastereoselectivity of hydrazo-ne alkylation. Asymmetric synthesis of α-amino-aldehydes

Alexakis, Alexandre; Lensen, Nathalie; Mangeney, Pierre

doi:10.1016/S0040-4039(00)92036-7

Scientific article

Letter

English

Chiral aminal templates 6. Diastereoselectivity of hydrazo-ne alkylation. Asymmetric synthesis of α-amino-aldehydes

ContributorsAlexakis, Alexandre; Lensen, Nathalie; Mangeney, Pierre

Published inTetrahedron letters, vol. 32, no. 9, p. 1171-1174

Publication date1991

Abstract

Glyoxal is efficiently transformed into the chiral animals bearing the hydrazone functionality 2a and 2b. These compounds react under complete diastereocontrol with various organolithium reagents, affording chiral hydrazines 3 -9. Reduction with Raney nickel leads to aminal protected a-aminoaldehydes, which, in turn, are easily hydrolyzed to the free chiral aldehydes (after tBoc protection of the amine).

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Not a UNIGE publication

Citation (ISO format)

ALEXAKIS, Alexandre, LENSEN, Nathalie, MANGENEY, Pierre. Chiral aminal templates 6. Diastereoselectivity of hydrazo-ne alkylation. Asymmetric synthesis of α-amino-aldehydes. In: Tetrahedron letters, 1991, vol. 32, n° 9, p. 1171–1174. doi: 10.1016/S0040-4039(00)92036-7

Article (Published version)

Identifiers

PID : unige:8084
DOI : 10.1016/S0040-4039(00)92036-7

Journal ISSN0040-4039

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Chiral aminal templates 6. Diastereoselectivity of hydrazo-ne alkylation. Asymmetric synthesis of α-amino-aldehydes

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