N-(9-(9-phenylfluorenyl))homoserine-derived cyclic sulfamidates:: Novel chiral educts for the synthesis of enantiopure γ-substituted α-amino acids

被引:50
作者
Atfani, M [1 ]
Wei, L [1 ]
Lubell, WD [1 ]
机构
[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
关键词
D O I
10.1021/ol016225b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] (4S)-tert-Butyl 2,2-dioxo-3-PhF-1,2,3-oxathiazainane-4-carboxylate reacted effectively with nitrogen, sulfur, and oxygen nucleophiles to provide enantiopure (> 97% ee) gamma -substituted alpha -amino acids.
引用
收藏
页码:2965 / 2968
页数:4
相关论文
共 26 条
[1]   ORGANOCUPRATES IN A NEW SYNTHESIS OF PURE ENANTIOMERIC AMINO-ACIDS [J].
BAJGROWICZ, JA ;
ELHALLAOUI, A ;
JACQUIER, R ;
PIGIERE, C ;
VIALLEFONT, P .
TETRAHEDRON, 1985, 41 (10) :1833-1843
[2]   CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS [J].
BALDWIN, JE ;
SPIVEY, AC ;
SCHOFIELD, CJ .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :881-884
[3]   THE FREE-RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE - A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE [J].
BARTON, DHR ;
CRICH, D ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
TETRAHEDRON, 1985, 41 (19) :4347-4357
[4]   MANIPULATION OF THE CARBOXYL GROUPS OF ALPHA-AMINO-ACIDS AND PEPTIDES USING RADICAL CHEMISTRY BASED ON ESTERS OF N-HYDROXY-2-THIOPYRIDONE [J].
BARTON, DHR ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
TETRAHEDRON, 1988, 44 (17) :5479-5486
[5]   SYNTHESIS OF OPTICALLY PURE PIPECOLATES FROM L-ASPARAGINE - APPLICATION TO THE TOTAL SYNTHESIS OF (+)-APOVINCAMINE THROUGH AMINO-ACID DECARBONYLATION AND IMINIUM ION CYCLIZATION [J].
CHRISTIE, BD ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1239-1246
[6]   Synthesis of N-Fmoc-alpha-amino acids carrying the four DNA nucleobases in the side chain. [J].
Ciapetti, P ;
Soccolini, F ;
Taddei, M .
TETRAHEDRON, 1997, 53 (03) :1167-1176
[7]   1,2,3-OXATHIAZOLIDINES - A NEW HETEROCYCLIC SYSTEM [J].
DEYRUP, JA ;
MOYER, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :175-&
[8]   Synthesis of 1,3-difunctionalized amine derivatives through selective C-H bond oxidation [J].
Espino, CG ;
Wehn, PM ;
Chow, J ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6935-6936
[9]   An olefination entry for the synthesis of enantiopure α,ω-diaminodicarboxylates and azabicyclo[X.Y.0] alkane amino acids [J].
Gosselin, F ;
Lubell, WD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7463-7471
[10]   NATURAL PRODUCT SYNTHESIS IN AGRICULTURAL CHEMISTRY .1. A NOVEL AND CONVENIENT ROUTE TO L-HOMOSERINE LACTONES AND L-PHOSPHINOTHRICIN FROM L-ASPARTIC ACID [J].
HOFFMANN, MG ;
ZEISS, HJ .
TETRAHEDRON LETTERS, 1992, 33 (19) :2669-2672