A NEW ELECTROPHILIC ALANINOL SYNTHON - A GENERAL-ROUTE TO OXAZOLIDINONES OF D-2-AMINO OR (R)-2-AMINO ALCOHOLS FROM L-SERINE

被引：38

作者：

SIBI, MP

RUTHERFORD, D

SHARMA, R

机构：

[1] Department of Chemistry, North Dakota State University, Fargo

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 13期

关键词：

D O I：

10.1039/p19940001675

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new electrophilic alaninol synthon, (S)-4-(4'-tolylsulfonyloxymethyl) oxazolidin-2-one, derived from serine, undergoes nucleophilic displacements with Gilman cuprates and/or Grignard/CuX reagents in high yield to provide (R)-4-substituted oxazolidinones.

引用

页码：1675 / 1678

页数：4

共 58 条

[1] SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE
ARNOLD, LD
MAY, RG
VEDERAS, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) : 2237 - 2241
[2] CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS
ARNOLD, LD
DROVER, JCG
VEDERAS, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4649 - 4659
[3] CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES
ARNOLD, LD
KALANTAR, TH
VEDERAS, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) : 7105 - 7109
[4] BAJGROWICZ JA, 1984, TETRAHEDRON LETT, V25, P2759, DOI 10.1016/S0040-4039(01)81283-1
[5] ORGANOCUPRATES IN A NEW SYNTHESIS OF PURE ENANTIOMERIC AMINO-ACIDS
BAJGROWICZ, JA
ELHALLAOUI, A
JACQUIER, R
PIGIERE, C
VIALLEFONT, P
[J]. TETRAHEDRON, 1985, 41 (10) : 1833 - 1843
[6] ASYMMETRIC AMINO-ACID SYNTHESIS - PREPARATION OF THE BETA-ANION DERIVED FROM ASPARTIC-ACID
BALDWIN, JE
MOLONEY, MG
NORTH, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04): : 833 - 834
[7] NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS
BALDWIN, JE
ADLINGTON, RM
ROBINSON, NG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) : 153 - 155
[8] AMINO-ACID SYNTHESIS VIA RING-OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
BALDWIN, JE
SPIVEY, AC
SCHOFIELD, CJ
SWEENEY, JB
[J]. TETRAHEDRON, 1993, 49 (28) : 6309 - 6330
[9] CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS
BALDWIN, JE
SPIVEY, AC
SCHOFIELD, CJ
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 881 - 884
[10] NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS
BALDWIN, JE
MOLONEY, MG
NORTH, M
[J]. TETRAHEDRON, 1989, 45 (19) : 6309 - 6318

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