Stereospecific Functionalization of Iodoaziridines via Unstabilized Aziridinyllithiums Generated by Iodine-Lithium Exchange

被引：12

作者：

Boultwood, Tom ^{[1
]}

Bull, James A. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

BETA-ALKOXY AZIRIDINES; ORGANOLITHIUM-MEDIATED CONVERSION; ASYMMETRIC-SYNTHESIS; REACTION OPTIMIZATION; ALLYLIC SULFONAMIDES; CATALYZED SYNTHESIS; C-SILYLAZIRIDINES; LITHIATION; HYDANTOINS; REACTIVITY;

D O I：

10.1021/ol501024y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium iodine exchange on alkyl- or aryl-substituted N-tosyliodoaziridines afforded unstabilized aziridinyllithiums, which were subsequently trapped at low temperatures with a range of carbon and heteroatom electrophiles affording cis-substituted aziridines exclusively. When using isocyanates as electrophiles, access to aziridine carboxamides or 1,3,5-trisubstituted hydantoins can be selected by control of reaction temperature.

引用

页码：2740 / 2743

页数：4

共 67 条

[1] Highly diastereoselective aziridination of imines with trimethylsilyldiazomethane.: Subsequent silyl substitution with electrophiles, ring opening, and metalation of C-silylaziridines -: A cornucopia of highly selective transformations [J].

Aggarwal, VK ;

Alonso, E ;

Ferrara, M ;

Spey, SE .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2335-2344

[2] Highly selective aziridination of imines using trimethylsilyldiazomethane and applications of C-silylaziridines in synthesis [J].

Aggarwal, VK ;

Ferrara, M .

ORGANIC LETTERS, 2000, 2 (25) :4107-4110

[3] THE MECHANISM OF THE LITHIUM HALOGEN INTERCHANGE REACTION - A REVIEW OF THE LITERATURE [J].

BAILEY, WF ;

PATRICIA, JJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 352 (1-2) :1-46

[4] THE HALOGEN/MAGNESIUM-EXCHANGE USING iPrMgCl.LiCl AND RELATED EXCHANGE REAGENTS [J].

Barl, Nadja M. ;

Werner, Veronika ;

Saemann, Christoph ;

Knochel, Paul .

HETEROCYCLES, 2014, 88 (02) :827-844

[5] INTRAMOLECULAR CYCLIZATIONS OF ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - CONVENIENT SYNTHESES OF 3-MEMBERED-RING, 5-MEMBERED-RING, AND 6-MEMBERED-RING HETEROCYCLIC NITROGEN-COMPOUNDS AND ELABORATIONS OF 3-MEMBERED RING-SYSTEMS [J].

BEAK, P ;

WU, SD ;

YUM, EK ;

JUN, YM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :276-277

[6] Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography [J].

Boultwood, Tom ;

Affron, Dominic P. ;

Bull, James A. .

JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2014, (87)

[7] Synthesis of cis-C-Iodo-N-Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography [J].

Boultwood, Tom ;

Affron, Dominic P. ;

Trowbridge, Aaron D. ;

Bull, James A. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13) :6632-6647

[8] CYCLIZATION OF DEPROTONATED 2-PHENYL-1-TOSYLAZIRIDINE - A SURPRISING EXAMPLE OF AN INTRAMOLECULAR NUCLEOPHILIC AROMATIC ADDITION [J].

BRETERNITZ, HJ ;

SCHAUMANN, E ;

ADIWIDJAJA, G .

TETRAHEDRON LETTERS, 1991, 32 (10) :1299-1302

[9] Highly cis-selective synthesis of iodo-aziridines using diiodomethyllithium and in situ generated N-Boc-imines [J].

Bull, James A. ;

Boultwood, Tom ;

Taylor, Thomas A. .

CHEMICAL COMMUNICATIONS, 2012, 48 (100) :12246-12248

[10] Directed ortho lithiation of N-alkylphenylaziridines [J].

Capriati, V ;

Florio, S ;

Luisi, R ;

Musio, B .

ORGANIC LETTERS, 2005, 7 (17) :3749-3752

← 1 2 3 4 5 6 7 →