General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation

被引：35

作者：

Matos, Priscilla Mendonca ^{[1
,2
]}

Lewis, William ^{[1
]}

Argent, Stephen P. ^{[1
]}

Moore, Jonathan C. ^{[1
]}

Stockman, Robert A. ^{[1
]}

机构：

[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England

[2] Minist Educ Brazil, CAPES Fdn, BR-70040020 Brasilia, DF, Brazil

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 07期

关键词：

CATALYZED NITRENE TRANSFER; ONE-POT SYNTHESIS; KINETIC RESOLUTION; ELECTROPHILIC NH; SULFOXIDES; AROYLATION; IMINATION; SULFIDES; ACCESS; SULFONIMIDAMIDES;

D O I：

10.1021/acs.orglett.0c00761

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile method for the synthesis of enantioen-riched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines.

引用

页码：2776 / 2780

页数：5

共 65 条

[1] Metal-Free Approach for the Synthesis of N-Aryl Sulfoximines via Aryne Intermediate [J].

Aithagani, Sravan Kumar ;

Dara, Saidulu ;

Munagala, Gurunadham ;

Aruri, Hariprasad ;

Yadav, Mahipal ;

Sharma, Shweta ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

ORGANIC LETTERS, 2015, 17 (22) :5547-5549

[2]

ANDERSEN KK, 1962, TETRAHEDRON LETT, P93

[3] OPTICALLY ACTIVE SULFOXIDES . SYNTHESIS + ROTATORY DISPERSION OF SOME DIARYL SULFOXIDES [J].

ANDERSEN, KK ;

FOLEY, JW ;

GAFFIELD, W ;

PAPANIKOLAU, NE ;

PERKINS, RI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5637-+

[4] Asymmetric Synthesis of Chiral Sulfoximines via the S-Arylation of Sulfinamides [J].

Aota, Yusuke ;

Kano, Taichi ;

Maruoka, Keiji .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (49) :19263-19268

[5] Asymmetric Synthesis of Chiral Sulfoximines through the S-Alkylation of Sulfinamides [J].

Aota, Yusuke ;

Kano, Taichi ;

Maruoka, Keiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (49) :17661-17665

[6] Sulfoximinocarbonylation of aryl halides using heterogeneous Pd/C catalyst [J].

Bala, Balasubramanian Devi ;

Sharma, Nidhi ;

Sekar, Govindasamy .

RSC ADVANCES, 2016, 6 (99) :97152-97159

[7]

Balasubramaniam S., 2018, MOJ BIORG ORG CHEM, V2, P93

[8] Sulfur imidations: access to sulfimides and sulfoximines [J].

Bizet, Vincent ;

Hendriks, Christine M. M. ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (11) :3378-3390

[9] Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines [J].

Bizet, Vincent ;

Buglioni, Laura ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) :5639-5642

[10] Fluorinated sulfoximines: syntheses, properties and applications [J].

Bizet, Vincent ;

Kowalczyk, Rafal ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2426-2438

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