Synthesis of 2-substituted dihydropyran 3-O-carbamates via combined metalation-Suzuki-Miyaura cross-coupling reactions

被引：16

作者：

Bower, JF ^{[1
]}

Guillaneux, D ^{[1
]}

Nguyen, T ^{[1
]}

Wong, PL ^{[1
]}

Snieckus, V ^{[1
]}

机构：

[1] Univ Waterloo, Guelph Waterloo Ctr Grad Work Chem, Waterloo, ON N2L 3G1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 05期

关键词：

D O I：

10.1021/jo971771x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 6-[(N,N-diethylcarbamoyl)oxy]-3,4-dihydro-2H-pyran (8) with t-BuLi followed by quench with a variety of electrophiles leads to 2-substituted products 9a-j (Table 2) in modest to good yields. The thereby obtained 2-boronic acid (11) and iodo (9j) derivatives undergo Suzuki-Migaura cross-coupling reactions to afford 2-aryl and -heteroaryl dihydropyran O-carbamates 12a-d in excellent yields.

引用

页码：1514 / 1518

页数：5

共 33 条

[1]

ADAM W, 1982, SYNTHESIS-STUTTGART, P322

[2] SEQUENTIAL DIRECTED ORTHO METALATION BORONIC ACID CROSS-COUPLING REACTIONS - A GENERAL REGIOSPECIFIC ROUTE TO OXYGENATED DIBENZO[B,D]PYRAN-6-ONES RELATED TO ELLAGIC ACID [J].

ALO, BI ;

KANDIL, A ;

PATIL, PA ;

SHARP, MJ ;

SIDDIQUI, MA ;

SNIECKUS, V ;

JOSEPHY, PD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3763-3768

[3] A STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED ALKENES .2. THE NICKEL-CATALYZED COUPLING OF GRIGNARD-REAGENTS WITH 6-ALKYL-3,4-DIHYDRO-2H-PYRANS AND ACYCLIC ENOL ETHERS [J].

ASHWORTH, PA ;

DIXON, NJ ;

KOCIENSKI, PJ ;

WADMAN, SN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3431-3438

[4] C-GLYCOSYL COMPOUNDS BIND TO RECEPTORS ON THE SURFACE OF ESCHERICHIA-COLI AND CAN TARGET PROTEINS TO THE ORGANISM [J].

BERTOZZI, C ;

BEDNARSKI, M .

CARBOHYDRATE RESEARCH, 1992, 223 :243-253

[5] PREPARATION AND REACTIVITY OF LITHIUM 1,4-DIOXENYL CUPRATES [J].

BLANCHOTCOURTOIS, V ;

HANNA, I .

TETRAHEDRON LETTERS, 1992, 33 (52) :8087-8090

[6]

BOWER JE, UNPUB

[7]

Brown D.S., 1991, ORG SYNTH, V70, P157

[8]

CASSON S, 1993, SYNTHESIS-STUTTGART, P1133

[9] REGIOSPECIFIC ENOLATES FROM TETRAHYDROPYRAN-3-ONE - SYNTHETIC EQUIVALENTS OF A THERMODYNAMICALLY AND KINETICALLY DISFAVOURED ENOLATE ISOMER [J].

COX, P ;

LISTER, S ;

GALLAGHER, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3151-3157

[10] CHEMISTRY, OCCURRENCE AND BIOSYNTHESIS OF C-GLYCOSYL COMPOUNDS IN PLANTS [J].

FRANZ, G ;

GRUN, M .

PLANTA MEDICA, 1983, 47 (03) :131-140

← 1 2 3 4 →