Synthesis of Methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate via a Hofmann Rearrangement Utilizing Trichloroisocyanuric Acid as an Oxidant

被引：39

作者：

Crane, Zackary D. ^{[1
]}

Nichols, Paul J. ^{[1
]}

Sammakia, Tarek ^{[1
]}

Stengel, Peter J. ^{[1
]}

机构：

[1] Array Bio Pharma Inc, Dept Proc Chem, Boulder, CO 80301 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 01期

关键词：

LEAD-TETRAACETATE; CONVENIENT REAGENT; SCHMIDT REACTION; AMIDES; INHIBITORS; CHLORINATION; AMINOLYSIS; PROTEASE; AMINES; AZIDES;

D O I：

10.1021/jo101504e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, atyl, benzyl, and nitro groups.

引用

页码：277 / 280

页数：4

共 58 条

[1]

ACOTT B, 1965, TETRAHEDRON LETT, P4039

[2] REACTION OF LEAD TETRA-ACETATE WITH PRIMARY AMIDES . FORMATION OF ACYLAMINES [J].

ACOTT, B ;

BECKWITH, AL .

CHEMICAL COMMUNICATIONS, 1965, (08) :161-&

[3] REACTIONS OF LEAD TETRAACETATE .2. FORMATION OF CARBAMIC ACID ESTERS FROM PRIMARY CARBOXAMIDES [J].

ACOTT, B ;

BECKWITH, AL ;

HASSANAL.A .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1968, 21 (01) :197-&

[4] Diastereoselective synthesis of cyclopropane amino acids using diazo compounds generated in situ [J].

Adams, LA ;

Aggarwal, VK ;

Bonnert, RV ;

Bressel, B ;

Cox, RJ ;

Shepherd, J ;

de Vicente, J ;

Walter, M ;

Whittingham, WG ;

Winn, CL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9433-9440

[5] N,O-Bis-(ethoxycarbonyl)hydroxylamine:: a convenient reagent for the Lossen transformation [J].

Anilkumar, R ;

Chandrasekhar, S ;

Sridhar, M .

TETRAHEDRON LETTERS, 2000, 41 (27) :5291-5293

[6]

[Anonymous], 2004, ORGANIC SYNTHESIS, VX, P549

[7]

[Anonymous], 1993, ORGANIC SYNTHESIS, VVIII, P132

[8] INTRAMOLECULAR SCHMIDT REACTION OF ALKYL AZIDES [J].

AUBE, J ;

MILLIGAN, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8965-8966

[9] THEORETICAL-STUDY OF THE BARRIER TO NITROGEN INVERSION IN N-CYANOFORMIMINE AND N-DIAZOFORMIMINE - MECHANISM OF THE SCHMIDT REACTION [J].

BACH, RD ;

WOLBER, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02) :239-245

[10] REACTIONS OF AMINES .14. AN OXIDATIVE REARRANGEMENT OF AMIDES [J].

BAUMGART.HE ;

STAKLIS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (05) :1141-&

← 1 2 3 4 5 6 →