9-BBN TRIFLATE MEDIATED STEREOSELECTIVE ALKYLATION OF 2-ALKYL IMIDAZOLINES WITH TETRAHYDROFURANS

被引：7

作者：

DALKO, PI ^{[1
]}

LANGLOIS, Y ^{[1
]}

机构：

[1] UNIV PARIS 11,ICMO,CNRS,SYNTHESE SUBST NAT LAB,BATIMENT 410,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)79135-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic attack of deprotonated imidazolines 3 or 4 on tetrahydrofuran derivatives in the presence of 9-BBN triflate can afford the corresponding alkylated products 7 with moderate to good stereoselectivities.

引用

页码：5213 / 5216

页数：4

共 16 条

[1] DIHYDROIMIDAZOLES IN SYNTHESIS - C-ALKYLATION OF 1-BENZYL-2-(ALPHA-LITHIOALKYL)-4,5-DIHYDROIMIDAZOLES AND A SYNTHESIS OF ALKANOIC ACIDS [J].

ANDERSON, MW ;

JONES, RCF ;

SAUNDERS, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (02) :205-209

[2] THE COPPER(I)-CATALYZED COUPLING OF GRIGNARD-REAGENTS WITH 5-LITHIO-2,3-DIHYDROFURAN AND 6-LITHIO-3,4-DIHYDRO-2H-PYRAN [J].

BARBER, C ;

BURY, P ;

KOCIENSKI, P ;

OSHEA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (22) :1595-1597

[3] B-BROMO-9-BORABICYCLO[3.3.1]NONANE - CONVENIENT AND SELECTIVE REAGENT FOR ETHER CLEAVAGE [J].

BHATT, MV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 156 (01) :221-226

[4] CLEAVAGE OF ETHERS [J].

BHATT, MV ;

KULKARNI, SU .

SYNTHESIS-STUTTGART, 1983, (04) :249-282

[5] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ACHIRAL ALLYLIC ESTERS [J].

COREY, EJ ;

LEE, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4026-4028

[6] A CHIRAL SOLVATING AGENT FOR DIRECT NMR ASSAY OF THE ENANTIOMERIC PURITY OF CARBOXYLIC-ACIDS [J].

FULWOOD, R ;

PARKER, D .

TETRAHEDRON-ASYMMETRY, 1992, 3 (01) :25-28

[7] AMIDE BOND ISOSTERES - IMIDAZOLINES IN PSEUDOPEPTIDE CHEMISTRY [J].

JONES, RCF ;

WARD, GJ .

TETRAHEDRON LETTERS, 1988, 29 (31) :3853-3856

[8] A NOVEL METHOD FOR THE SYNTHESIS OF SYMMETRICAL VICINAL TERTIARY AND SECONDARY DIAMINES [J].

KATRITZKY, AR ;

FAN, WQ ;

FU, C .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3209-3213

[9] IMPROVED OPTICAL RESOLUTION OF R-STAR, R-STAR N,N'-DIMETHYL 1,2-DIPHENYL ETHYLENE DIAMINE [J].

MANGENEY, P ;

GROJEAN, F ;

ALEXAKIS, A ;

NORMANT, JF .

TETRAHEDRON LETTERS, 1988, 29 (22) :2675-2676

[10] METHODOLOGY FOR THE CONSTRUCTION OF QUATERNARY CARBON CENTERS [J].

MARTIN, SF .

TETRAHEDRON, 1980, 36 (04) :419-460

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