Highly diastereoselective radical cyclisations of chiral sulfinimines

被引：23

作者：

Rochette, Elise M. ^{[1
]}

Lewis, William ^{[1
]}

Dossetter, Al G. ^{[2
]}

Stockman, Robert A. ^{[1
]}

机构：

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

[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 82期

基金：

英国工程与自然科学研究理事会;

关键词：

ASYMMETRIC-SYNTHESIS; ALDIMINES; EFFICIENT; ALCOHOLS; IMINES;

D O I：

10.1039/c3cc45452e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral amines are formed by the highly diastereoselective intramolecular addition of alkyl and aryl radicals onto chiral mesityl sulfinimines.

引用

页码：9395 / 9397

页数：3

共 26 条

[1] Asymmetric radical addition of ethers to enantiopure N-p-toluenesulfinyl aldimines, mediated by dimethylzinc-air [J].

Akindele, Tito ;

Yamamoto, Yasutomo ;

Maekawa, Masaru ;

Umeki, Hiroyuki ;

Yamada, Ken-ichi ;

Tomioka, Kiyoshi .

ORGANIC LETTERS, 2006, 8 (25) :5729-5732

[2] Stereoselective Radical Addition of an Acetal to Sterically Tuned Enantiomerically Pure N-Sulfinyl Imines [J].

Akindele, Tito ;

Yamada, Ken-ichi ;

Sejima, Takumi ;

Maekawa, Masaru ;

Yamamoto, Yasutomo ;

Nakano, Mayu ;

Tomioka, Kiyoshi .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (02) :265-269

[3] Carbocyclization by radical closure onto O-trityl oximes:: Dramatic effect of diphenyl diselenide [J].

Clive, Derrick L. J. ;

Pham, Mai P. ;

Subedi, Rajendra .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (09) :2713-2717

[4] Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide [J].

Davis, FA ;

Ramachandar, T ;

Wu, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6894-6898

[5] Intermolecular Alkyl Radical Additions to Enantiopure N-tert-Butanesulfinyl Aldimines [J].

Fernandez-Salas, Jose A. ;

Carmen Maestro, M. ;

Mercedes Rodriguez-Fernandez, M. ;

Garcia-Ruano, Jose L. ;

Alonso, Ines .

ORGANIC LETTERS, 2013, 15 (07) :1658-1661

[6] Potassium carbonate-silica: a highly effective stationary phase for the chromatographic removal of organotin impurities [J].

Harrowven, David C. ;

Curran, Dennis P. ;

Kostiuk, Sarah L. ;

Wallis-Guy, Ian L. ;

Whiting, Sally ;

Stenning, Kerri J. ;

Tang, Bencan ;

Packard, Emma ;

Nanson, Lana .

CHEMICAL COMMUNICATIONS, 2010, 46 (34) :6335-6337

[7]

Lacote E., 1998, CR HEBD ACAD SCI, P191

[8] Concise asymmetric synthesis of (-)-deoxoprosophylline [J].

Liu, Ru-Cheng ;

Wei, Jin-Hu ;

Wei, Bang-Guo ;

Lin, Guo-Qiang .

TETRAHEDRON-ASYMMETRY, 2008, 19 (23) :2731-2734

[9] Concise asymmetric synthesis of (+)-CP-99,994 and (+)-L-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols [J].

Liu, Run-Hua ;

Fang, Kai ;

Wang, Bing ;

Xu, Ming-Hua ;

Lin, Guo-Qiang .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3307-3310

[10] Escape from Flatland 2: complexity and promiscuity [J].

Lovering, Frank .

MEDCHEMCOMM, 2013, 4 (03) :515-519

← 1 2 3 →