HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION MEDIATED BY A CHIRAL AUXILIARY DERIVED FROM AMINO INDANOL - THE ROLE OF CONFORMATION ON DIASTEREOSELECTIVITY

被引：50

作者：

DAVIES, IW ^{[1
]}

SENANAYAKE, CH ^{[1
]}

CASTONGUAY, L ^{[1
]}

LARSEN, RD ^{[1
]}

VERHOEVEN, TR ^{[1
]}

REIDER, PJ ^{[1
]}

机构：

[1] MERCK & CO INC,RES LABS,DEPT MOLEC DESIGN & DIVERS,RAHWAY,NJ 07065

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 42期

关键词：

D O I：

10.1016/0040-4039(95)01584-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxazolidinone 2 derived from amino indanol 1 functions as a very efficient chiral auxiliary for the Diels-Alder reaction. The effect of conformation has been explored using a range of constrained phenyl glycinol analogues.

引用

页码：7619 / 7622

页数：4

共 11 条

[1] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES
EVANS, DA
CHAPMAN, KT
BISAHA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) : 1238 - 1256
[2] TRANSITION-STATE PI-SOLVATION BY AROMATIC RINGS - AN ELECTRONIC CONTRIBUTION TO DIELS-ALDER REACTION DIASTEREOSELECTIVITY
EVANS, DA
CHAPMAN, KT
HUNG, DT
KAWAGUCHI, AT
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1184 - 1186
[3] DIASTEREOFACIAL SELECTIVITY IN INTRAMOLECULAR DIELS-ALDER REACTIONS OF CHIRAL TRIENE-N-ACYLOXAZOLIDONES
EVANS, DA
CHAPMAN, KT
BISAHA, J
[J]. TETRAHEDRON LETTERS, 1984, 25 (37) : 4071 - 4074
[4] GHOSH AK, 1992, J CHEM SOC CHEM COMM, P1673, DOI 10.1039/C39920001673
[5] HALGREN, 1995, J COMP CHEM
[6] LITHIUM-INITIATED IMIDE FORMATION - A SIMPLE METHOD FOR N-ACYLATION OF 2-OXAZOLIDINONES AND BORNANE-2,10-SULTAM
HO, GJ
MATHRE, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) : 2271 - 2273
[7] HOLLOWAY, 1995, J MED CHEM, V38, P305
[8] DIASTEREOSELECTIVE SYN-EPOXIDATION OF 2-ALKYL-4-ENAMIDES TO EPOXYAMIDES - SYNTHESIS OF THE MERCK HIV-1 PROTEASE INHIBITOR EPOXIDE INTERMEDIATE
MALIGRES, PE
UPADHYAY, V
ROSSEN, K
CIANCIOSI, SJ
PURICK, RM
ENG, KK
REAMER, RA
ASKIN, D
VOLANTE, RP
REIDER, PJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (13) : 2195 - 2198
[9] THE BEHAVIOR OF INDENE OXIDE IN THE RITTER REACTION - A SIMPLE ROUTE TO CIS-AMINOINDANOL
SENANAYAKE, CH
ROBERTS, FE
DIMICHELE, LM
RYAN, KM
LIU, J
FREDENBURGH, LE
FOSTER, BS
DOUGLAS, AW
LARSEN, RD
VERHOEVEN, TR
REIDER, PJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (23) : 3993 - 3996
[10] REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESES OF CYCLIC CHIRAL CIS-AMINO ALCOHOLS FROM 1,2-DIOLS OR EPOXIDES
SENANAYAKE, CH
DIMICHELE, LM
LIU, J
FREDENBURGH, LE
RYAN, KM
ROBERTS, FE
LARSEN, RD
VERHOEVEN, TR
REIDER, PJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (42) : 7615 - 7618

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