CATALYTIC ENANTIOSELECTIVE DIELS-ALDER ADDITION TO FURAN PROVIDES A DIRECT SYNTHETIC ROUTE TO MANY CHIRAL NATURAL-PRODUCTS

被引:147
作者
COREY, EJ
LOH, TP
机构
[1] Department of Chemistry, Harvard University, Cambridge
关键词
D O I
10.1016/S0040-4039(00)60594-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An oxazaborolidine derived from N-tosyl (alphaS,betaR)-beta-methyltryptophan (1)catalyzes the Diels-Alder reaction of 2-bromoacrolein and furan with 96:4 enantioselectivity, leading to an efficient synthesis of numerous chiral 7-oxabicyclo[2.2.1]heptene derivatives.
引用
收藏
页码:3979 / 3982
页数:4
相关论文
共 15 条
[1]   1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].
COREY, EJ ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967
[2]   THE ORIGIN OF GREATER THAN 200/1 ENANTIOSELECTIVITY IN A CATALYTIC DIELS-ALDER REACTION AS REVEALED BY PHYSICAL AND CHEMICAL STUDIES [J].
COREY, EJ ;
LOH, TP ;
ROPER, TD ;
AZIMIOARA, MD ;
NOE, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8290-8292
[3]   SYNTHESIS OF 9,11-EPOXY-9A-HOMOPROSTAGLANDIN ANALOGS [J].
EGGELTE, TA ;
KONING, HD ;
HUISMAN, HO .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (09) :980-989
[4]  
JUST G, 1976, TETRAHEDRON LETT, P1063
[5]   C-NUCLEOSIDES AND RELATED COMPOUNDS .12. SYNTHESIS OF CARBOCYCLIC ANALOGS OF D,L-6-AZAPSEUDOURIDINE, 2-THIO-6-AZAPSEUDOURIDINE, AND PYRAZOFURIN A - CYCLIZATION OF SEMICARBAZONES OF ALPHA-KETO ESTERS [J].
JUST, G ;
KIM, S .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (03) :427-434
[6]   C-NUCLEOSIDES AND RELATED COMPOUNDS .8. SYNTHESIS OF D,L-2'-DEOXYSHOWDOMYCIN (1D) [J].
JUST, G ;
LIM, MI .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (16) :2993-2997
[7]   HIGH-PRESSURE DIELS-ALDER REACTIONS OF FURANS WITH ALPHA-CHLOROXYACRYLONITRILE AND ALPHA-ACETOXYACRYLONITRILE [J].
KOTSUKI, H ;
NISHIZAWA, H .
HETEROCYCLES, 1981, 16 (08) :1287-1290
[8]  
MURAI A, 1901, J CHEM SOC CHEM COMM, P221
[9]   MUSCARINIC RECEPTORS - DERIVATIVES OF 7-OXABICYCLO[2.2.1]HEPTANE [J].
NELSON, WL ;
ALLEN, DR ;
VINCENZI, FF .
JOURNAL OF MEDICINAL CHEMISTRY, 1971, 14 (08) :698-&
[10]   PSEUDO-SUGARS .3. ALTERNATIVE SYNTHESIS OF PENTA-N,O-ACETYL-DL-VALIDAMINE AND ITS ANALOGS [J].
OGAWA, S ;
KASAHARA, I ;
SUAMI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (01) :118-123