Catalytic, asymmetric cyanohydrin synthesis mediated by lanthanide(III) chloride pybox complexes

被引：66

作者：

Aspinall, HC ^{[1
]}

Greeves, N ^{[1
]}

Smith, PM ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Donnan & Robert Robinson Labs, Liverpool L69 7ZD, Merseyside, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 09期

关键词：

asymmetric synthesis; catalysis; cyanohydrins; lanthanides;

D O I：

10.1016/S0040-4039(98)02685-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Complexes formed between lanthanide trichlorides and 2,6-bis(substituted-2-oxazolin-2 yl)pyridine (pybox) ligands are effective catalysts for the enantioselective addition of trimethylsilylcyanide (TMSCN) to a range of aldehydes. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1763 / 1766

页数：4

相关论文

共 19 条

[1] A BMPD-yttrium isopropoxide complex: Highly efficient chiral Lewis acid catalyst for asymmetric silylcyanation [J].

Abiko, A ;

Wang, GQ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2264-2265

[2] AN APPROACH TO THE SYNTHESIS OF BACTOBOLIN AND THE TOTAL SYNTHESIS OF N-ACETYLACTINOBOLAMINE - SOME REMARKABLY STABLE HEMIACETALS [J].

ASKIN, D ;

ANGST, C ;

DANISHEFSKY, S .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :622-635

[3]

EFFENBERGER F, 1994, ANGEW CHEM INT EDIT, V33, P1555, DOI 10.1002/anie.199415551

[4] C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis [J].

Ghosh, AK ;

Packiarajan, M ;

Cappiello, J .

TETRAHEDRON-ASYMMETRY, 1998, 9 (01) :1-45

[5] Enzymatic cleavage and formation of cyanohydrins: a reaction of biological and synthetic relevance [J].

Griengl, H ;

Hickel, A ;

Johnson, DV ;

Kratky, C ;

Schmidt, M ;

Schwab, H .

CHEMICAL COMMUNICATIONS, 1997, (20) :1933-1940

[6] Enantioselective addition of trimethylsilyl cyanide to aldehydes induced by a new chiral Ti(IV) complex [J].

Hwang, CD ;

Hwang, DR ;

Uang, BJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6762-6763

[7] NEW CHIRAL RUTHENIUM BIS(OXAZOLINYL)PYRIDINE CATALYST - EFFICIENT ASYMMETRIC CYCLOPROPANATION OF OLEFINS WITH DIAZOACETATES [J].

NISHIYAMA, H ;

ITOH, Y ;

MATSUMOTO, H ;

PARK, SB ;

ITOH, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2223-2224

[8]

NORTH M, 1995, COMPREHENSIVE ORGANI, V3, pCH8

[9] LANTHANOID(III) ALKOXIDES AS NOVEL CATALYSTS FOR A RAPID TRANSHYDROCYANATION FROM ACETONE CYANOHYDRIN TO ALDEHYDES AND KETONES [J].

OHNO, H ;

MORI, A ;

INOUE, S .

CHEMISTRY LETTERS, 1993, (02) :375-378

[10] Enantioselective trimethylsilylcyanation of aldehydes catalyzed by chiral lanthanoid alkoxides [J].

Qian, CT ;

Zhu, CJ ;

Huang, TS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (14) :2131-2132