Aminosubstituted tert-butylsulfinylferrocenes as a new family of chiral ligands:: asymmetric addition of diethylzinc to aldehydes

被引：37

作者：

Priego, J ^{[1
]}

Mancheño, OG ^{[1
]}

Cabrera, S ^{[1
]}

Carretero, JC ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 19期

关键词：

D O I：

10.1039/b105962a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ready access to a new family of planar chiral ferrocenes, the (R-Fc,R-S)-2-amino substituted 1-tert-butylsulfinylferrocenes, is described; in the case of the sulfonamide series enantioselectivities of up to 96% were obtained in the addition of Et2Zn to aromatic aldehydes.

引用

页码：2026 / 2027

页数：2

共 23 条

[1]

[Anonymous], COMPREHENSIVE ASYMME

[2] On the role of planar chirality in asymmetric catalysis:: A study toward appropriate ferrocene ligands for diethylzinc additions [J].

Bolm, C ;

Muñiz-Fernández, K ;

Seger, A ;

Raabe, G ;

Günther, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7860-7867

[3] The 2-(N,N-dimethylamino)phenylsulfinyl group as an efficient chiral auxiliary in intramolecular Heck reactions [J].

Buezo, ND ;

Mancheño, OG ;

Carretero, JC .

ORGANIC LETTERS, 2000, 2 (10) :1451-1454

[4] CATALYTIC ACTIVITY OF CHIRAL BETA-HYDROXYSULFOXIDES IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE [J].

CARRENO, MC ;

RUANO, JLG ;

MAESTRO, MC ;

CABREJAS, LMM .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :727-734

[5] Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].

Cogan, DA ;

Liu, GC ;

Kim, KJ ;

Backes, BJ ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019

[6] Chiral ligands derived from abrine.: Part 6:: Importance of a bulky N-alkyl group in indole-containing chiral β-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes [J].

Dai, WM ;

Zhu, HJ ;

Hao, XJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (11) :2315-2337

[7] HIGHLY ENANTIOSELECTIVE OXIDATION OF FERROCENYL SULFIDES [J].

DITER, P ;

SAMUEL, O ;

TAUDIEN, S ;

KAGAN, HB .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :549-552

[8]

Hayashi T., 1995, FERROCENES HOMOGENEO

[9] Chiral β-phosphino sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions [J].

Hiroi, K ;

Suzuki, Y ;

Kawagishi, R .

TETRAHEDRON LETTERS, 1999, 40 (04) :715-718

[10] New chiral sulfoxide ligands possessing a phosphano or phosphanoamino functionality in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions [J].

Hiroi, K ;

Suzuki, Y ;

Abe, I ;

Kawagishi, R .

TETRAHEDRON, 2000, 56 (27) :4701-4710

← 1 2 3 →