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

Authors
Lensen, Nathalie
Mangeney, Pierre
Published in Tetrahedron Letters. 1991, vol. 32, no. 9, p. 1171-1174
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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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. https://archive-ouverte.unige.ch/unige:8084

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Deposited on : 2010-06-21

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