Cobalt(II)-azabis(oxazoline)-catalyzed conjugate reduction of α,β-unsaturated carbonyl compounds

被引：48

作者：

Geiger, C ^{[1
]}

Kreitmeier, P ^{[1
]}

Reiser, O ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 2-3期

关键词：

azabis(oxazolines); cobalt; conjugate reduction; transition metals; alpha; beta-unsaturated amides; beta-unsaturated esters;

D O I：

10.1002/adsc.200404295

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Azabis(oxazolines) prove to be superior ligands for the enantioselective, cobalt(II)-catalyzed conjugate reduction of alpha,beta-unsaturated carbonyl compounds with sodium borohydride. beta-Trisubstituted a,p-unsaturated esters and amides as well as gamma-butenolides are readily converted to their corresponding saturated counterparts with enantioselectivities up to 97% ee.

引用

页码：249 / 254

页数：6

共 26 条

[1] Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst [J].

Appella, DH ;

Moritani, Y ;

Shintani, R ;

Ferreira, EM ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9473-9474

[2] Paraconic acids -: The natural products from Lichen symbiont [J].

Bandichhor, R ;

Nosse, B ;

Reiser, O .

NATURAL PRODUCTS SYNTHESIS I: TARGETS METHODS CONCEPTS, 2005, 243 :43-72

[3] Enantioselective synthesis of paraconic acids [J].

Chhor, RB ;

Nosse, B ;

Sörgel, S ;

Böhn, C ;

Seitz, M ;

Reiser, O .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :260-270

[4]

Connolly J. D., 1991, DICT TERPENOIDS, V1, P476

[5]

EVANS D, COMMUNICATION

[6]

FERRABOSCHI P, 1987, J CHEM SOC P1, P1741

[7] The importance of complex stability for asymmetric copper-catalyzed cyclopropanations in [emim][OTf] ionic liquid:: the bis(oxazoline)-azabis(oxazoline) case [J].

Fraile, JM ;

García, JI ;

Herrerías, CI ;

Mayoral, JA ;

Reiser, O ;

Vaultier, M .

TETRAHEDRON LETTERS, 2004, 45 (36) :6765-6768

[8] The role of binding constants in the efficiency of chiral catalysts immobilized by electrostatic interactions:: The case of azabis(oxazoline)Copper complexes [J].

Fraile, JM ;

García, JI ;

Herrerías, CI ;

Mayoral, JA ;

Reiser, O ;

Socuéllamos, A ;

Werner, H .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :2997-3005

[9] Immobilisation of bis(oxazoline) copper complexes on clays and nanocomposites.: Influence of different parameters on activity and selectivity [J].

Fraile, JM ;

García, JI ;

Harmer, MA ;

Herrerías, CI ;

Mayoral, JA ;

Reiser, O ;

Werner, H .

JOURNAL OF MATERIALS CHEMISTRY, 2002, 12 (11) :3290-3295

[10] Aza-bis(oxazolines): New chiral ligands for asymmetric catalysis [J].

Glos, M ;

Reiser, O .

ORGANIC LETTERS, 2000, 2 (14) :2045-2048

← 1 2 3 →