Intramolecular cyclopropanation of unsaturated terminal aziridines

被引：25

作者：

Hodgson, DM ^{[1
]}

Humphreys, PG ^{[1
]}

Ward, JG ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 05期

关键词：

D O I：

10.1021/ol060101n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regio- and stereoselective deprotonation of bishomoallylic terminal N-Bus (Bus = tert-butylsulfonyl)-protected aziridines generate aziridinyl anions that undergo diastereoselective intramolecular cyclopropanation giving trans-2-aminobicyclo[3.1.0]hexanes in good to excellent yields.

引用

页码：995 / 998

页数：4

共 41 条

[21]

Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V2, P607

[22] Bromine-catalyzed aziridination of olefins. A rare example of atom-transfer redox catalysis by a main group element [J].

Jeong, JU ;

Tao, B ;

Sagasser, I ;

Henniges, H ;

Sharpless, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (27) :6844-6845

[23] General catalytic synthesis of highly enantiomerically enriched terminal aziridines from racemic epoxides [J].

Kim, SK ;

Jacobsen, EN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3952-3954

[24] Aziridine-allylsilane-mediated synthesis of exocyclic γ-amino olefins and azabicyclo[x.y.1]-systems [J].

Lapinsky, DJ ;

Bergmeier, SC .

TETRAHEDRON, 2002, 58 (35) :7109-7117

[25] Synthesis of novel apio carbocyclic nucleoside analogues as selective A3 adenosine receptor agonists [J].

Lee, JA ;

Moon, HR ;

Kim, HO ;

Kim, KR ;

Lee, KM ;

Kim, BT ;

Hwang, KJ ;

Chun, MW ;

Jacobson, KA ;

Jeong, LS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5006-5013

[26] Synthesis and lithiation of oxazolinylaziridines:: the N-substituent effect [J].

Luisi, R ;

Capriati, V ;

Florio, S ;

Di Cunto, P ;

Musio, B .

TETRAHEDRON, 2005, 61 (13) :3251-3260

[27] Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides? [J].

Marquez, VE ;

Siddiqui, MA ;

Ezzitouni, A ;

Russ, P ;

Wang, JY ;

Wagner, RW ;

Matteucci, MD .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3739-3747

[28] Discovery of bicycloalkyl urea melanin concentrating hormone receptor antagonists: Orally efficacious antiobesity therapeutics [J].

McBriar, MD ;

Guzik, H ;

Xu, R ;

Paruchova, J ;

Li, SJ ;

Palani, A ;

Clader, JW ;

Greenlee, WJ ;

Hawes, BE ;

Kowalski, TJ ;

O'Neill, K ;

Spar, B ;

Weig, B .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (07) :2274-2277

[29]

MOSHE A, 1981, EUR J MED CHEM, V16, P199

[30] Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds [J].

Müller, P ;

Fruit, C .

CHEMICAL REVIEWS, 2003, 103 (08) :2905-2919

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