Enantioselective Bronsted acid catalyzed addition reactions of methyleneaminopyrrolidine to imines

被引：46

作者：

Dixon, DJ

Tillman, AL

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

SYNLETT | 2005年 / 17期

关键词：

organocatalysis; hydrogen bond donor; imines; hydrazone; asymmetric synthesis;

D O I：

10.1055/s-2005-917098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new series of BINOL-derived multidentate Bronsted acid catalysts has been developed for the enantioselective addition of the d(1)-synthon, methyleneaminopyrrolidine, to N-Boc imines, yielding the versatile, protected alpha-aminohydrazone intermediates in moderate to good ee.

引用

收藏

页码：2635 / 2638

页数：4

相关论文

共 22 条

[1] Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].

Brochu, MP ;

Brown, SP ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109

[2] The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].

Brown, SP ;

Brochu, MP ;

Sinz, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809

[3] Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst [J].

Corey, EJ ;

Grogan, MJ .

ORGANIC LETTERS, 1999, 1 (01) :157-160

[4] Formaldehyde dialkylhydrazones as neutral formyl anion and cyanide equivalents: Nucleophilic addition to conjugated enones [J].

Diez, E ;

Fernandez, R ;

Gasch, C ;

Lassaletta, JM ;

Llera, JM ;

MartinZamora, E ;

Vazquez, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :5144-5155

[5]

Enders D, 1996, SYNTHESIS-STUTTGART, P48

[6]

Fernandez R, 1996, SYNTHESIS-STUTTGART, P627

[7]

Fernández R, 2001, SYNLETT, P1158

[8] Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst [J].

Huang, Y ;

Unni, AK ;

Thadani, AN ;

Rawal, VH .

NATURE, 2003, 424 (6945) :146-146

[9] RETRACTED: Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide (Retracted article. See JUN, 2023) [J].

Iyer, MS ;

Gigstad, KM ;

Namdev, ND ;

Lipton, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4910-4911

[10] Formaldehyde dimethylhydrazone: A new neutral reagent for nucleophilic hydroformylation and hydrocyanation [J].

Lassaletta, JM ;

Fernandez, R ;

Gasch, C ;

Vazquez, J .

TETRAHEDRON, 1996, 52 (27) :9143-9160