Preparation of enantiomerically pure protected unsaturated α-amino acids from a new serine derived zinc–copper reagent
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 4,p. 319-320
- https://doi.org/10.1039/c39920000319
Abstract
Treatment of the iodoalanine derived zinc reagent 1 with Knochel's soluble copper salt (CuCN·2LiCl) allows the preparation of a reactive copper reagent 2 which couples in moderate to good yield with allyl halides to give protected unsaturated α-amino acids in a single step from easily available precursors.Keywords
This publication has 12 references indexed in Scilit:
- Preparation and reactions of zinc and copper organometallics bearing acidic hydrogensThe Journal of Organic Chemistry, 1991
- Asymmetric synthesis of 2,6-diamino-6-(hydroxymethyl)pimelic acid: assignment of stereochemistryJournal of the American Chemical Society, 1991
- The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, .alpha.,.beta.-unsaturated ketones, and allylic, aryl, and vinyl halidesThe Journal of Organic Chemistry, 1991
- An Approach to the Synthesis of Enantiomerically Pure Hydroxylated α-Amino Acids Using Zinc Homoenolate ChemistrySynlett, 1990
- Copper(I)‐Promoted Michael‐Addition Reaction of Organozincs of Esters, Nitriles, and α‐Amino AcidsAngewandte Chemie International Edition in English, 1989
- A new direct method for the synthesis of enantiomerically pure protected α-amino acidsJournal of the Chemical Society, Chemical Communications, 1989
- Unsaturated ester synthesis via copper(I)-catalyzed allylation of zinc estersThe Journal of Organic Chemistry, 1987
- Radical reactions in synthesis: carbon–carbon bond formation from 2-substituted allyl trialkyl stannanesJournal of the Chemical Society, Chemical Communications, 1986
- Allene transfer reactions. A new synthesis of terminal allenesJournal of the Chemical Society, Chemical Communications, 1984
- A naturally-occurring allenic amino acidTetrahedron Letters, 1968