Asymmetric Synthesis of α,α-Difluoro-β-amino Acid Derivatives from Enantiomerically Pure N-tert-Butylsulfinimines
- 22 October 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (23) , 8276-8279
- https://doi.org/10.1021/jo0259313
Abstract
Addition of the Reformatsky reagent derived from ethyl bromodifluoroacetate to alkyl- and aryl-substituted N-tert-butylsulfinimines furnishes beta-tert-butylsulfinamyl-beta-substituted alpha,alpha-difluoroproponiates in diastereomeric ratios ranging from 80:20 to 95:5. The diastereomers are easily separated and the enantiomerically pure, protected beta-amino esters are readily transformed to the corresponding acid, amide, and amine derivatives as useful synthons for medicinal chemistry targets.Keywords
This publication has 10 references indexed in Scilit:
- Synthesis and Antifungal Activity of Rhodopeptin Analogues. 2. Modification of the West Amino Acid MoietyOrganic Letters, 2000
- Enantioselective Synthesis of α,α-Difluoro-β-amino Acid and 3,3-Difluoroazetidin-2-one via the Reformatsky-Type Reaction of Ethyl Bromodifluoroacetate with Chiral 1,3-OxazolidinesThe Journal of Organic Chemistry, 1999
- Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl iminesTetrahedron, 1999
- Catalytic Asymmetric Oxidation oftert-Butyl Disulfide. Synthesis oftert-Butanesulfinamides,tert-Butyl Sulfoxides, andtert-ButanesulfiniminesJournal of the American Chemical Society, 1998
- Asymmetric synthesis of amino acids using sulfinimines (thiooxime S-oxides)Chemical Society Reviews, 1998
- Difluoromethyleneketone retroamide, a versatile concept of inactivation of proteolytic enzymesTetrahedron, 1996
- Synthesis of a peptidyl 2,2-difluoro-3-aminopropionateBioorganic & Medicinal Chemistry Letters, 1992
- Inhibition of serine proteases by peptidyl fluoromethyl ketonesBiochemistry, 1986
- C-Metallated reformatsky intermediates. Structure and reactivity.Tetrahedron, 1984
- Reformatsky intermediate. A C-metallated species.Tetrahedron Letters, 1982