Stereoselective nucleophilic monofluoromethylation of N-(tert-butanesulfinyl)imines with fluoromethyl phenyl sulfone

被引：97

作者：

Li, Y ^{[1
]}

Ni, CF ^{[1
]}

Liu, J ^{[1
]}

Zhang, LJ ^{[1
]}

Zheng, J ^{[1
]}

Zhu, LG ^{[1
]}

Hu, JB ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 08期

关键词：

D O I：

10.1021/ol060322t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective nucleophilic monofluoromethylation of (R)-(tert-butanesulfinyl)imines with fluoromethyl phenyl sulfone was achieved to afford alpha-monofluoromethylamines with a nonchelation-controlled stereoselectivity mode. By using the same chemistry, (R)-(tert-butanesulfinyl)imines bearing a terminal tosylate (M) group can be converted to alpha-monofluoromethylated cyclic secondary amines with high stereoselectivity.

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页码：1693 / 1696

页数：4

相关论文

共 19 条

[1]

ALYERNHE G, 1980, J FLUORINE CHEM, V16, P526

[2]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[3] SYNTHESIS OF (E)-4-AMINO-2,5-HEXADIENOIC ACID AND (E)-4-AMINO-5-FLUORO-2-PENTENOIC ACID - IRREVERSIBLE INHIBITORS OF 4-AMINOBUTYRATE-2-OXOGLUTARATE AMINOTRANSFERASE [J].

BEY, P ;

GERHART, F ;

JUNG, M .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2835-2838

[4] ALPHA-(FLUOROMETHYL)DEHYDROORNITHINE AND ALPHA-(FLUOROMETHYL)DEHYDROPUTRESCINE ANALOGS AS IRREVERSIBLE INHIBITORS OF ORNITHINE DECARBOXYLASE [J].

BEY, P ;

GERHART, F ;

VANDORSSELAER, V ;

DANZIN, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (11) :1551-1556

[5] Stereoselective synthesis of the antibacterial 3-fluoro-D-alanine [J].

Bravo, P ;

Cavicchio, G ;

Crucianelli, M ;

Poggiali, A ;

Zanda, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (16) :2811-2815

[6] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[7] Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the α2-adrenoceptor [J].

Grunewald, GL ;

Caldwell, TM ;

Li, QF ;

Slavica, M ;

Criscione, KR ;

Borchardt, RT ;

Wang, W .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (18) :3588-3601

[8] A NOVEL AND EFFICIENT SYNTHESIS OF FLUOROMETHYL PHENYL SULFONE AND ITS USE AS A FLUOROMETHYL WITTIG EQUIVALENT [J].

INBASEKARAN, M ;

PEET, NP ;

MCCARTHY, JR ;

LETOURNEAU, ME .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) :678-679

[9] Asymmetric synthesis of α-monofluoromethyl- and α-difluoromethylbenzylamines through regioselective hydrogenolysis [J].

Kanai, M ;

Ueda, K ;

Yasumoto, M ;

Kuriyama, Y ;

Inomiya, K ;

Ootsuka, T ;

Katsuhara, Y ;

Higashiyama, K ;

Ishii, A .

JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (03) :377-383

[10] SELECTIVE FLUORINATION OF HYDROXY AMINES AND HYDROXY AMINO-ACIDS WITH SULFUR TETRAFLUORIDE IN LIQUID-HYDROGEN FLUORIDE [J].

KOLLONITSCH, J ;

MARBURG, S ;

PERKINS, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (25) :3808-3809