BINOLAM, a recoverable chiral ligand for bifunctional enantioselective catalysis:: The asymmetric synthesis of cyanohydrins

被引：105

作者：

Casas, J

Nájera, C

Sansano, JM

Saá, JM

机构：

[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Illes Balears, Dept Quim, E-07071 Palma de Mallorca, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 15期

关键词：

D O I：

10.1021/ol0262338

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new bifunctional catalytic system based on a monometallic aluminum complex is used for the efficient enantioselective cyanation of aldehydes. The ligand (S)- or (R)-2,2'-bis(diethylaminomethyl)-substituted binaphthol (BINOLAM) used is recovered for recycling. This methodology is used for the synthesis of a precursor of epothilone A.

引用

收藏

页码：2589 / 2592

页数：4

相关论文

共 44 条

[1] The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes [J].

Belokon, YN ;

Caveda-Cepas, S ;

Green, B ;

Ikonnikov, NS ;

Krustalev, VN ;

Larichev, VS ;

Moscalenko, MA ;

North, M ;

Orizu, C ;

Tararov, VI ;

Tasinazzo, M ;

Timofeeva, GI ;

Yashkina, LV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :3968-3973

[2] Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies [J].

Bode, JW ;

Carreira, EM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6410-6424

[3] ON THE MECHANISM OF THE FORMATION OF "S(-)-(1,1'-BINAPHTHALENE)-2,2'-DIOL VIA COPPER(II)AMINE COMPLEXES [J].

BRUSSEE, J ;

GROENENDIJK, JLG ;

TEKOPPELE, JM ;

JANSEN, ACA .

TETRAHEDRON, 1985, 41 (16) :3313-3319

[4] Enantioselective synthesis of (S)-α-methylphenylalanine using (S)-BINOLAMs as new phase-transfer catalysts [J].

Casas, J ;

Nájera, C ;

Sansano, JM ;

González, J ;

Saá, JM ;

Vega, M .

TETRAHEDRON-ASYMMETRY, 2001, 12 (05) :699-702

[5]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[6]

2-Z

[7] HOST-GUEST COMPLEXATION .8. MACROCYCLIC POLYETHERS SHAPED BY 2 RIGID SUBSTITUTED DINAPHTHYL OR DITETRALYL UNITS [J].

CRAM, DJ ;

HELGESON, RC ;

PEACOCK, SC ;

KAPLAN, LJ ;

DOMEIER, LA ;

MOREAU, P ;

KOGA, K ;

MAYER, JM ;

CHAO, Y ;

SIEGEL, MG ;

HOFFMAN, DH ;

SOGAH, GDY .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1930-1946

[8]

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

[9]

FERINGA B, 1977, TETRAHEDRON LETT, P4447

[10] Recoverable catalysts. Ultimate goals, criteria of evaluation, and the green chemistry interface [J].

Gladysz, JA .

PURE AND APPLIED CHEMISTRY, 2001, 73 (08) :1319-1324

← 1 2 3 4 5 →