Practical synthesis of sultams via sulfonamide dianion alkylation: Application to the synthesis of chiral sultams

被引：48

作者：

Lee, JM ^{[1
]}

Zhong, YL ^{[1
]}

Reamer, RA ^{[1
]}

Askin, D ^{[1
]}

机构：

[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 22期

关键词：

D O I：

10.1021/ol0356183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[graphics] A practical synthesis of sultams was developed via intramolecular sulfonamide dianion alkylation. This method has been applied toward the synthesis of chiral sultams, which are synthetically valuable as chiral auxiliaries.

引用

页码：4175 / 4177

页数：3

共 32 条

[1] The evaluation of chiral benzosultams as auxiliaries in asymmetric azidation reaction [J].

Ahn, KH ;

Kim, SK ;

Ham, C .

TETRAHEDRON LETTERS, 1998, 39 (35) :6321-6322

[2] Practical synthesis of chiral sultam auxiliaries: 3-substituted-1,2-benzisothiazoline 1,1-dioxides [J].

Ahn, KH ;

Ham, C ;

Kim, SK ;

Cho, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7047-7048

[3] Synthesis of chiral benzosultams: 3-functionalized 1,2-benzisothiazoline 1,1-dioxides [J].

Ahn, KH ;

Baek, HH ;

Lee, SJ ;

Cho, CW .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7690-7696

[4] Perhydropyrrolo[1,2-A]indole synthesis: Diastereoselection in an intramolecular conjugate addition of an amine to a 1,4-cyclohexadienone [J].

Bland, D ;

Hart, DJ ;

Lacoutiere, S .

TETRAHEDRON, 1997, 53 (26) :8871-8880

[5]

BLISS AD, 1963, J ORG CHEM, V28, P3537, DOI 10.1021/jo01047a065

[6]

BOWMAN WC, 1979, TXB PHARM, pCH34

[7] Stereoselective synthesis of homochiral annulated sultams via intramolecular cycloaddition reactions [J].

Chiacchio, U ;

Corsaro, A ;

Rescifina, A ;

Bkaithan, M ;

Grassi, G ;

Piperno, A ;

Privitera, T ;

Romeo, G .

TETRAHEDRON, 2001, 57 (16) :3425-3433

[8] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[9] SELECTIVE MONOFLUORINATION AND DIFLUORINATION OF ENOLATES [J].

DIFFERDING, E ;

RUEGG, GM ;

LANG, RW .

TETRAHEDRON LETTERS, 1991, 32 (15) :1779-1782

[10] NEW FLUORINATING REAGENTS .2. PREPARATION AND SYNTHETIC APPLICATION OF A SACCHARIN DERIVED N-FLUOROSULTAM [J].

DIFFERDING, E ;

LANG, RW .

HELVETICA CHIMICA ACTA, 1989, 72 (06) :1248-1252

← 1 2 3 4 →