Diastereoselective synthesis of pyrrolidine derivatives via a one-pot nitro-Mannich/hydroamination cascade using base and gold catalysis

被引：19

作者：

Duris, Andrej ^{[1
]}

Barber, David M. ^{[1
]}

Sanganee, Hitesh J. ^{[2
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

[2] AstraZeneca R&D, New Opportun iMed, Alderley Pk SK10 4GT, Cheshire, England

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 27期

基金：

英国工程与自然科学研究理事会;

关键词：

INTRAMOLECULAR HYDROAMINATION; INTERMOLECULAR HYDROAMINATION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AZOMETHINE YLIDES; ATOM ECONOMY; ALLENES; (-)-NAKADOMARIN; REPLACEMENT; METATHESIS;

D O I：

10.1039/c3cc40729b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient one-pot nitro-Mannich/hydroamination cascade reaction for the synthesis of substituted pyrrolidines bearing three stereocentres is reported. Proceeding under the control of a combination of base and gold(I) catalysts, the cascade reaction affords the pyrrolidine products in high yields with good to excellent diastereoselectivities.

引用

页码：2777 / 2779

页数：3

共 42 条

[1] Asymmetric hydroamination of non-activated carbon-carbon multiple bonds [J].

Aillaud, Isabelle ;

Collin, Jacqueline ;

Hannedouche, Jerome ;

Schulz, Emmanuelle .

DALTON TRANSACTIONS, 2007, (44) :5105-5118

[2] Stereoselective Synthesis of Densely Functionalized Pyrrolidin-2-ones by a Conjugate Addition/Nitro-Mannich/Lactamization Reaction [J].

Anderson, James C. ;

Horsfall, Lisa R. ;

Kalogirou, Andreas S. ;

Mills, Matthew R. ;

Stepney, Gregory J. ;

Tizzard, Graham J. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14) :6186-6198

[3] Enantioselective Conjugate Addition Nitro-Mannich Reactions: Solvent Controlled Synthesis of Acyclic anti- and syn-β-Nitroamines with Three Contiguous Stereocenters [J].

Anderson, James C. ;

Stepney, Gregory J. ;

Mills, Matthew R. ;

Horsfall, Lisa R. ;

Blake, Alexander J. ;

Lewis, William .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :1961-1971

[4] One-Pot Catalytic Enantioselective Synthesis of Tetrahydropyridines via a Nitro-Mannich/Hydroamination Cascade [J].

Barber, David M. ;

Sanganee, Hitesh J. ;

Dixon, Darren J. .

ORGANIC LETTERS, 2012, 14 (20) :5290-5293

[5] One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis [J].

Barber, David M. ;

Sanganee, Hitesh ;

Dixon, Darren J. .

CHEMICAL COMMUNICATIONS, 2011, 47 (15) :4379-4381

[6] Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes [J].

Butler, Kristina L. ;

Tragni, Michele ;

Widenhoefer, Ross A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5175-5178

[7] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

[8] Gold(I)-Catalyzed Intermolecular Hydroamination of Allenes with Arylamines [J].

Duncan, Alethea N. ;

Widenhoefer, Ross A. .

SYNLETT, 2010, (03) :419-422

[9] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[10]

Grondal C, 2010, NAT CHEM, V2, P167, DOI [10.1038/NCHEM.539, 10.1038/nchem.539]

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