DRAMATIC SOLVENTS EFFECTS ON THE ENANTIOSELECTIVITY OF CHIRAL OXAZABOROLIDINE CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITIONS OF NITRONES WITH KETENE ACETALS

被引：95

作者：

SEERDEN, JPG ^{[1
]}

KUYPERS, MMM ^{[1
]}

SCHEEREN, HW ^{[1
]}

机构：

[1] CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,NSR CTR MOLEC STRUCT DESIGN & SYNTH,6525 ED NIJMEGEN,NETHERLANDS

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 06期

关键词：

D O I：

10.1016/0957-4166(95)00177-Q

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselectivity of the chiral oxazaborolidine catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones with 1,1-dialkonypropenes can be controlled by the ct-side-chain substituent in the catalyst and the solvent. Remarkable reversal of enantioselectivity is achieved for catalysts having aryl substituents in the cr-side-chain by addition of ligand-like solvents. Both enantiomers of a chiral beta-amino ester have been prepared in two catalytic steps.

引用

页码：1441 / 1450

页数：10

共 79 条

[1]

Tufariello, 1,3-Dipolar Cycloadditions Chemistry, 2, pp. 83-168, (1984)

[2]

Confalone, Huie, Org. React., 36, pp. 1-173, (1988)

[3]

Balasubramanian, Org. Prep. Proc. Int., (1985)

[4]

Black, Crozier, Davis, 1,3-Dipolar Cycloaddition Reactions of Nitrones, Synthesis, pp. 205-221, (1975)

[5]

Annunziata, Cinquini, Cozzi, Raimondi, Gazz. Chim. Ital., 119, pp. 253-269, (1989)

[6]

Mulzer, Naturstoffe via 1,3-dipolare Cycloaddition I, Nachrichten aus Chemie, Technik und Laboratorium, 32, pp. 882-887, (1984)

[7]

Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, pp. 1-47, (1988)

[8]

Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, pp. 75-89, (1988)

[9]

Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, pp. 129-327, (1988)

[10]

Dopp, Dopp, Houben-Weyl-Methoden der Organischen Chemie, vol E14b, (1990)

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