WATER-PROMOTED CLAISEN SIGMATROPIC REARRANGEMENT USING GLYCO-ORGANIC SUBSTRATES - CHIRAL AUXILIARY-MEDIATED INDUCTION

被引：25

作者：

LUBINEAU, A ^{[1
]}

AUGE, J ^{[1
]}

BELLANGER, N ^{[1
]}

CAILLEBOURDIN, S ^{[1
]}

机构：

[1] INST CHIM MOLEC ORSAY,CNRS,CHIM ORGAN MULTIFONCTIONNELLE LAB,BT 420,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(00)97566-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Claisen sigmatropic rearrangement with glyco-organic substrates is greatly accelerated in water. Moreover, the ability of glucose to function as a chiral auxiliary is illustrated in the preparation of 4-pentene-1,3-diol, obtained for the first time in pure enantiomeric form. © 1990.

引用

页码：4147 / 4150

页数：4

共 19 条

[1] THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS
BLECHERT, S
[J]. SYNTHESIS-STUTTGART, 1989, (02): : 71 - 82
[2] EFFECT OF POLAR-SOLVENTS ON THE RATES OF CLAISEN REARRANGEMENTS - ASSESSMENT OF IONIC CHARACTER
BRANDES, E
GRIECO, PA
GAJEWSKI, JJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) : 515 - 516
[3] VOLUME CHANGE OF ACTIVATION IN CLAISEN AND CURTIUS REARRANGEMENTS
BROWER, KR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (21) : 4370 - &
[4] SYNTHESIS AND CLAISEN REARRANGEMENT OF ALKOXYALLYL ENOL ETHERS - EVIDENCE FOR A DIPOLAR TRANSITION-STATE
COATES, RM
ROGERS, BD
HOBBS, SJ
PECK, DR
CURRAN, DP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1160 - 1170
[5] THE CONFORMATIONAL EQUILIBRIUM OF CHORISMATE IN SOLUTION - IMPLICATIONS FOR THE MECHANISM OF THE NONENZYMATIC AND THE ENZYME-CATALYZED REARRANGEMENT OF CHORISMATE TO PREPHENATE
COPLEY, SD
KNOWLES, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) : 5008 - 5013
[6] ON THE MECHANISM OF REARRANGEMENT OF CHORISMIC ACID AND RELATED-COMPOUNDS
GAJEWSKI, JJ
JURAYJ, J
KIMBROUGH, DR
GANDE, ME
GANEM, B
CARPENTER, BK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1170 - 1186
[7] WATER AS A SOLVENT FOR THE CLAISEN REARRANGEMENT - PRACTICAL IMPLICATIONS FOR SYNTHETIC ORGANIC-CHEMISTRY
GRIECO, PA
BRANDES, EB
MCCANN, S
CLARK, JD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) : 5849 - 5851
[8] HILL RK, 1984, ASYMMETRIC SYNTHESIS, V3
[9] WATER-PROMOTED ORGANIC-REACTIONS - ALDOL REACTION OF SILYL ENOL ETHERS WITH CARBONYL-COMPOUNDS UNDER ATMOSPHERIC-PRESSURE AND NEUTRAL CONDITIONS
LUBINEAU, A
MEYER, E
[J]. TETRAHEDRON, 1988, 44 (19) : 6065 - 6070
[10] WATER-PROMOTED ORGANIC-REACTIONS - ALDOL REACTION UNDER NEUTRAL CONDITIONS
LUBINEAU, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11) : 2142 - 2144

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