Asymmetric Allenylation of N -Acylhydrazones with Propargyltrichlorosilane Catalyzed by Helical Chiral 2,2' -Bipyridine N -Monoxide

被引：0

作者：

Xu, Changgong ^{[1
]}

Nader, Phillip ^{[1
]}

Xavier, Jonathan ^{[1
]}

Takenaka, Norito ^{[1
]}

机构：

[1] Florida Inst Technol, Dept Biomed & Chem Engn & Sci, Chem Program, 150 West Univ Blvd, Melbourne, FL 32901 USA

来源：

SYNLETT | 2023年 / 34卷 / 20期

基金：

美国国家卫生研究院;

关键词：

azahelicene; organocatalysis; asymmetric synthesis; propargyltrichlorosilane; acylhydrazone; ENANTIOSELECTIVE SYNTHESIS; REGIOSPECIFIC ADDITION; SELECTIVE FORMATION; ALDEHYDES; HOMOALLENYLAMIDES; PROPARGYLSILANES; PROPARGYLATION; KETONES; ALLENES;

D O I：

10.1055/s-0042-1751478

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(M)-Helicene-derived 2,2'-bipyridine N-monoxide catalyzed the allenylation of N-acylhydrazones with propargyltrichlorosilane with excellent regioselectivity and moderate-to-good enantioselectivity. This study represents the first catalytic asymmetric allenylation of acylhydrazones.

引用

收藏

页码：2461 / 2464

页数：4

相关论文

共 30 条

[1] Helical Chiral 2,2′-Bipyridine N- Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane [J].

Chen, Jinshui ;

Captain, Burjor ;

Takenaka, Norito .

ORGANIC LETTERS, 2011, 13 (07) :1654-1657

[2] Pyridylalanine (Pal)-Peptide Catalyzed Enantioselective Allenoate Additions to N-Acyl Imines [J].

Cowen, Bryan J. ;

Saunders, Lindsey B. ;

Miller, Scott J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6105-+

[3] Ir-Catalyzed Enantioconvergent Synthesis of Diversely Protected Allenylic Amines Employing Ammonia Surrogates [J].

Glatz, Fabian ;

Petrone, David A. ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (38) :16404-16408

[4]

Hashimoto T, 2013, NAT CHEM, V5, P240, DOI [10.1038/NCHEM.1567, 10.1038/nchem.1567]

[5] Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones [J].

Hirabayashi, R ;

Ogawa, C ;

Sugiura, M ;

Kobayashi, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9493-9499

[6] Synthesis and properties of allenic natural products and pharmaceuticals [J].

Hoffmann-Röder, A ;

Krause, N .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) :1196-1216

[7] A Catalytic Asymmetric Borono Variant of Hosomi-Sakurai Reactions with N,O-Aminals [J].

Huang, Yi-Yong ;

Chakrabarti, Ananya ;

Morita, Naohide ;

Schneider, Uwe ;

Kobayashi, Shu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11121-11124

[8] Asymmetric allenylation of aliphatic aldehydes catalyzed by a chiral formamide [J].

Iseki, K ;

Kuroki, Y ;

Kobayashi, Y .

TETRAHEDRON-ASYMMETRY, 1998, 9 (16) :2889-2894

[9] Catalytic, enantioselective propargyl- and allenylation reactions of α-imino ester [J].

Kagoshima, H ;

Uzawa, T ;

Akiyama, T .

CHEMISTRY LETTERS, 2002, (03) :298-299

[10] SELECTIVE FORMATION OF PROPARGYLSILANES AND ALLENYLSILANES AND THEIR REACTIONS WITH ALDEHYDES FOR THE PREPARATION OF HOMOPROPARGYLIC AND ALLENIC ALCOHOLS [J].

KOBAYASHI, S ;

NISHIO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (23) :6392-6393