Enantioselective pinacol coupling of aldehydes mediated and catalyzed by chiral titanium complexes

被引：80

作者：

Bensari, A

Renaud, JL

Riant, O

机构：

[1] Catholic Univ Louvain, Lab Chim Organ & Med, Dept Chim, B-1348 Louvain, Belgium

[2] Univ Paris 11, Inst Chim Mol Orsay, Lab Catalyse Mol, F-91405 Orsay, France

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 24期

关键词：

D O I：

10.1021/ol016664a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Starting from easily available chiral Schiff bases, a straightforward synthesis of air-stable titanium(IV) complexes was devised. Asymmetric pinacol coupling of aromatic aldehydes mediated and catalyzed by the corresponding low valent complexes afforded the chiral diols with high yields and enantioselectivities up to 91%.

引用

页码：3863 / 3865

页数：3

共 31 条

[11] 2-Y
[12] Reagent-controlled transition-metal-catalyzed radical reactions
Gansäuer, A
Bluhm, H
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 2771 - 2788
[13] Novel concept for efficient transition-metal-catalyzed reactions:: A highly diastereoselective titanocene-catalyzed pinacol coupling under buffered protic conditions
Gansäuer, A
Bauer, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) : 2070 - 2071
[14] Gansauer A, 1997, SYNLETT, P363
[15] Groth U, 2000, ANGEW CHEM INT EDIT, V39, P574, DOI 10.1002/(SICI)1521-3773(20000204)39:3<574::AID-ANIE574>3.0.CO
[16] 2-O
[17] Structural studies of the low-valent titanium "solution": What goes on in the pinacol coupling reaction?
Hashimoto, Y
Mizuno, U
Matsuoka, H
Miyahara, T
Takakura, M
Yoshimoto, M
Oshima, K
Utimoto, K
Matsubara, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (07) : 1503 - 1504
[18] Mischmetall:: An efficient and low cost coreductant for catalytic reactions of samarium diiodide
Hélion, F
Namy, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) : 2944 - 2946
[19] Hirao T, 2000, SYNLETT, P1658
[20] A catalytic system consisting of vanadium, chlorosilane, and aluminum metal in the stereoselective pinacol coupling reaction of benzaldehyde derivatives
Hirao, T
Hatano, B
Imamoto, Y
Ogawa, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) : 7665 - 7667

← 1 2 3 4 →