HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER ADDITION PROMOTED BY A CHIRAL BIS(OXAZOLINE)-MAGNESIUM COMPLEX

被引：263

作者：

COREY, EJ

ISHIHARA, K

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)61781-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The new chiral bis(oxazoline) ligand 8 has been synthesized from (S)-phenylglycine and has been shown to form effective catalysts for enantioselective Diels-Alder addition in combination with ferric iodide, magnesium iodide or magnesium tetraphenylborate. Catalytic activation of the dienophile, 3-acryloyl-1,3-oxazolidine-2-one (4), in the magnesium system is proposed to involve tetrahedrally coordinated magnesium in a dipositive complex (10).

引用

页码：6807 / 6810

页数：4

共 5 条

[1] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX
COREY, EJ
IMAI, N
ZHANG, HY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 728 - 729
[2] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS
EVANS, DA
WOERPEL, KA
HINMAN, MM
FAUL, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 726 - 728
[3] ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS - BIS-OXAZOLINE COPPER-COMPLEXES
LOWENTHAL, RE
ABIKO, A
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (42) : 6005 - 6008
[4] ASYMMETRIC COPPER-CATALYZED CYCLOPROPANATION OF TRISUBSTITUTED AND UNSYMMETRICAL CIS-1,2-DISUBSTITUTED OLEFINS - MODIFIED BIS-OXAZOLINE LIGANDS
LOWENTHAL, RE
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (50) : 7373 - 7376
[5] HIGHLY ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH CHIRAL AND C2-SYMMETRICAL BIS(OXAZOLINYL)PYRIDINE-RHODIUM CATALYSTS
NISHIYAMA, H
KONDO, M
NAKAMURA, T
ITOH, K
[J]. ORGANOMETALLICS, 1991, 10 (02) : 500 - 508

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