CHIROSPECIFIC SYNTHESIS OF (1S,3R)-1-AMINO-3-(HYDROXYMETHYL)CYCLOPENTANE, A PRECURSOR FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS - INTRAMOLECULAR AZIRIDINE CYCLIZATIONS

被引:32
作者
BERGMEIER, SC [1 ]
LEE, WK [1 ]
RAPOPORT, H [1 ]
机构
[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720
关键词
D O I
10.1021/jo00070a050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:5019 / 5022
页数:4
相关论文
共 26 条
[1]   THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ONEIL, IA ;
SCHOFIELD, C ;
SPIVEY, AC ;
SWEENEY, JB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1852-1854
[2]   CHIROSPECIFIC SYNTHESIS OF (1S,3R)-1-AMINO-3-(HYDROXYMETHYL)CYCLOPENTANE, PRECURSOR FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS - DIECKMANN CYCLIZATION WITH AN ALPHA-AMINO-ACID [J].
BERGMEIER, SC ;
COBAS, AA ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2369-2376
[3]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[4]   SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].
BORTHWICK, AD ;
BIGGADIKE, K .
TETRAHEDRON, 1992, 48 (04) :571-623
[5]  
BOUAYAD Z, 1991, J HETEROCYCLIC CHEM, V28, P1757
[6]   DIASTEREOSPECIFIC SYNTHESIS OF DIAZIRIDINES FROM D-MANNITOL - ACCESS TO CHIRAL ALPHA-AMINO-ACIDS [J].
DUREAULT, A ;
GRECK, C ;
DEPEZAY, JC .
TETRAHEDRON LETTERS, 1986, 27 (35) :4157-4160
[7]   NUCLEOPHILIC OPENING OF CHIRAL BIS(AZIRIDINES) - A ROUTE TO ENANTIOMERICALLY PURE ALPHA-AMINO ALDEHYDES OR ACIDS AND POLYSUBSTITUTED PIPERIDINES [J].
DUREAULT, A ;
TRANCHEPAIN, I ;
DEPEZAY, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5324-5330
[8]   BF3-ETHERATE PROMOTED ALKYLATION OF AZIRIDINES WITH ORGANOCOPPER REAGENTS - A NEW SYNTHESIS OF AMINES [J].
EIS, MJ ;
GANEM, B .
TETRAHEDRON LETTERS, 1985, 26 (09) :1153-1156
[9]  
GHOSH NN, 1975, INDIAN J CHEM, V13, P596
[10]   CHEMISTRY OF CARBANIONS .6. STEREOCHEMISTRY OF WITTIG REACTION WITH STABILIZED YLIDS [J].
HOUSE, HO ;
JONES, VK ;
FRANK, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (11) :3327-&