Synthesis of α-Benzyloxyannino-γ-butyrolactones via a Polar Radical Crossover Cycloaddition Reaction

被引：49

作者：

Cavanaugh, Cortney L. ^{[1
]}

Nicewicz, David A. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

美国国家科学基金会;

关键词：

AMINO-ACIDS; HOMOSERINE LACTONE; DERIVATIVES; CONVENIENT; ALKENES;

D O I：

10.1021/acs.orglett.5b03113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct catalytic synthesis of substituted alpha-benzyloxyamino-gamma-butyrolactones is reported, starting from simple oxime acids and alkenes. The substituted O-benzyloxime acid starting materials are cyclized with oxidizable alkenes, via Polar Radical Crossover Cycloaddition (PRCC) reactions. The catalytic reaction is carried out using the Fukuzumi acridinium photooxidant and substoichiometric amounts of a redox-active cocatalyst. The utility of this method has been demonstrated through the use of 3 oxime acids and 19 oxidizable olefins.

引用

页码：6082 / 6085

页数：4

共 25 条

[1]

AGAMI C, 1992, SYNLETT, P847

[2] Direct lactonization of α-amino γ,δ-unsaturated carboxylic acid esters via olefin activation: stereo- and regioselective production of homoserine lactone scaffolds having contiguous stereocenters [J].

Aslam, Nayyar Ahmad ;

Babu, Srinivasarao Arulananda .

TETRAHEDRON, 2014, 70 (37) :6402-6419

[3] A CONVENIENT NEW SYNTHESIS OF HOMOSERINE LACTONE [J].

BALDWIN, JE ;

NORTH, M ;

FLINN, A .

TETRAHEDRON LETTERS, 1987, 28 (27) :3167-3168

[4] NEW SYNTHESIS OF AMINO-ACIDS .2. AMIDOALKYLATION OF OLEFINS WITH GLYOXYLIC-ACID DERIVATIVES [J].

BENISHAI, D ;

MOSHENBERG, R ;

ALTMAN, J .

TETRAHEDRON, 1977, 33 (12) :1533-1542

[5]

Clive D. L. J., 1997, J CHEM SOC CHEM COMM, P549

[6] FORMATION OF CARBON CARBON BONDS BY RING-CLOSURE OF BETA-PHENYLSELENOCROTONATES [J].

CLIVE, DLJ ;

BEAULIEU, PL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) :307-309

[7] AMINO ACID INTERMEDIATES - ALPHA-AMINO-GAMMA-LACTONES [J].

FILLMAN, J ;

ALBERTSON, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (01) :171-174

[8] Electron-transfer state of 9-mesityl-10-methylacridinium ion with a much longer lifetime and higher energy than that of the natural photosynthetic reaction center [J].

Fukuzumi, S ;

Kotani, H ;

Ohkubo, K ;

Ogo, S ;

Tkachenko, NV ;

Lemmetyinen, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1600-1601

[9] Synthesis of α-amino γ-butyrolactone derivatives by aziridination of α-ylidene γ-butyrolactones [J].

Gasperi, T ;

Loreto, MA ;

Tardella, PA ;

Veri, E .

TETRAHEDRON LETTERS, 2003, 44 (27) :4953-4956

[10] Amide and Amine Nucleophiles in Polar Radical Crossover Cycloadditions: Synthesis of γ-Lactams and Pyrrolidines [J].

Gesmundo, Nathan J. ;

Grandjean, Jean-Marc M. ;

Nicewicz, David A. .

ORGANIC LETTERS, 2015, 17 (05) :1316-1319

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