Highly diastereoselective allylic azide formation and isomerization.: Synthesis of 3(2′-amino)-β-lactams

被引：36

作者：

Cardillo, G ^{[1
]}

Fabbroni, S ^{[1
]}

Gentilucci, L ^{[1
]}

Perciaccante, R ^{[1
]}

Piccinelli, F ^{[1
]}

Tolomelli, A ^{[1
]}

机构：

[1] Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 04期

关键词：

D O I：

10.1021/ol047815n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective anti S(N)2' attack of NaN3 to 3-alkenyl-3-bromo-azetidin-2-ones gave a mixture of diastereomeric azides in fast equilibrium. The [3,3]-sigmatropic rearrangement of allylic azides occurred with complete stereocontrol, allowing the equilibrium to be directed preferentially toward the (E)- or (Z)-isomer, useful precursors of 3(2'-amino)-beta-lactams.

引用

页码：533 / 536

页数：4

共 32 条

[1] Synthesis of optically active spiro-β-lactams by cycloadditions to α-alkylidene-β-lactams [J].

Anklam, S ;

Liebscher, J .

TETRAHEDRON, 1998, 54 (23) :6369-6384

[2] STEREOCHEMISTRY OF THE CONCERTED SN2' REACTION OF 3-CHLOROPROPENE - A THEORETICAL-STUDY [J].

BACH, RD ;

WOLBER, GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1352-1357

[3] SYNTHETIC STUDIES ON TABTOXIN - SYNTHESIS OF A NATURALLY-OCCURRING INHIBITOR OF GLUTAMINE-SYNTHETASE, TABTOXININE-BETA-LACTAM, AND ANALOGS [J].

BALDWIN, JE ;

OTSUKA, M ;

WALLACE, PM .

TETRAHEDRON, 1986, 42 (12) :3097-3110

[4]

Banert K, 2000, EUR J ORG CHEM, V2000, P257

[5] Zinc metal-promoted nucleophilic addition of azetidin-2-ones to aldehydes and nitriles [J].

Benfatti, F ;

Cardillo, G ;

Fabbroni, S ;

Gentilucci, L ;

Perciaccante, R ;

Piccinelli, F ;

Tolomelli, A .

SYNTHESIS-STUTTGART, 2005, (01) :61-70

[6]

BOSE AK, 1971, TETRAHEDRON LETT, P3167

[7] ORIGIN OF PI-FACIAL STEREOSELECTIVITY IN ADDITIONS TO PI-BONDS - GENERALITY OF THE ANTI-PERIPLANAR EFFECT [J].

CARAMELLA, P ;

RONDAN, NG ;

PADDONROW, MN ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2438-2440

[8] Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition [J].

Cardillo, G ;

Fabbroni, S ;

Gentilucci, L ;

Perciaccante, R ;

Piccinelli, F ;

Tolomelli, A .

TETRAHEDRON, 2004, 60 (23) :5031-5040

[9] α-Bromo-β,γ-unsaturated ketenes for the synthesis of α-benzylamino-β,γ-unsaturated acids [J].

Cardillo, G ;

Fabbroni, S ;

Gentilucci, L ;

Perciaccante, R ;

Tolomelli, A .

TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :593-601

[10]

CARDILLO G, 1995, SYNLETT, P1131

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