Asymmetric induction of the lodolactonization reaction of α-sulfurated γ-unsaturated amides

被引：37

作者：

Blot, V ^{[1
]}

Reboul, V ^{[1
]}

Metzner, P ^{[1
]}

机构：

[1] Univ Caen, Lab Chim Mol & Thioorgan, CNRS, UMR 6507,ENSICAEN, F-14050 Caen, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 04期

关键词：

D O I：

10.1021/jo035488b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-asymmetric iodolactonization reaction of enantiopure alpha-sulfurated gamma-unsaturated amides has been investigated. With sulfinyl and sulfonyl groups, a poorly stereoselective reaction was observed, whereas with a sulfanyl moiety, the diastereoselectivity can be high as 96:4. The role of the oxygen atom on the sulfur moiety is discussed.

引用

页码：1196 / 1201

页数：6

共 31 条

[1] Stereocontrolled synthesis of (2S*,3R*,4R*)-4-hydroxy-3-methylproline using a silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement [J].

Anderson, JC ;

Flaherty, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (03) :267-269

[2]

[Anonymous], REV HETEROATAOM CHEM

[3] OXIDATIVE RADICAL CYCLIZATION OF (OMEGA-IODOALKYL)INDOLES AND PYRROLES - SYNTHESIS OF (-)-MONOMORINE AND 3 DIASTEREOMERS [J].

ARTIS, DR ;

CHO, IS ;

JAIMEFIGUEROA, S ;

MUCHOWSKI, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2456-2466

[4] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].

CHAMBERLIN, AR ;

MULHOLLAND, RL ;

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677

[5] IODOCYCLIZATION OF ALLYLIC ALCOHOL DERIVATIVES CONTAINING INTERNAL NUCLEOPHILES - CONTROL OF STEREOSELECTIVITY BY SUBSTITUENTS IN THE ACYCLIC PRECURSORS [J].

CHAMBERLIN, AR ;

DEZUBE, M ;

DUSSAULT, P ;

MCMILLS, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5819-5825

[6] Stereocontrolled iodolactonization of acyclic olefinic amides [J].

Ha, HJ ;

Lee, SY ;

Park, YS .

SYNTHETIC COMMUNICATIONS, 2000, 30 (20) :3645-3650

[7] Reagent-controlled stereoselective iodolactonizations [J].

Haas, J ;

Piguel, S ;

Wirth, T .

ORGANIC LETTERS, 2002, 4 (02) :297-300

[8] RAPID AND MILD DEOXYGENATION OF ORGANOHETEROATOM OXIDES WITH THE EFFICIENT ELECTRON-TRANSFER SYSTEM SMI2 TETRAHYDROFURAN HEXAMETHYLPHOSPHORIC TRIAMIDE [J].

HANDA, Y ;

INANAGA, J ;

YAMAGUCHI, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (05) :298-299

[9]

KANTLEHNER W, 1980, LIEBIGS ANN CHEM, P1677

[10] A FACILE ALPHA-IODINATION REACTION OF UNSATURATED AMIDES [J].

KITAGAWA, O ;

HANANO, T ;

HIRATA, T ;

INOUE, T ;

TAGUCHI, T .

TETRAHEDRON LETTERS, 1992, 33 (10) :1299-1302

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