Stereochemistry of palladium-catalyzed asymmetric transformation of chiral 2-alkynyl sulfinates into allenyl sulfones

被引：18

作者：

Hiroi, K ^{[1
]}

Kato, F ^{[1
]}

Nakasato, H ^{[1
]}

机构：

[1] Tohoku Coll Pharm, Dept Synth Organ Chem, Sendai, Miyagi 9818558, Japan

来源：

CHEMISTRY LETTERS | 1998年 / 06期

关键词：

D O I：

10.1246/cl.1998.553

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active 2-alkynyl p-toluenesulfinates, possessing chirality on both the alpha-carbons of the 2-alkynyl groups and the sulfur atoms of the sulfinates, were readily transformed into chiral allenyl sulfones with high stereospecificity in good yields by treatment with palladium acetate. The stereochemistry of the transformation was determined and the plausible mechanistic pathway is proposed.

引用

页码：553 / 554

页数：2

共 11 条

[1] [2,3]-SIGMATROPIC REARRANGEMENT OF PROPARGYL BENZENESULFINATES TO ALLENYL PHENYL SULFONES [J].

BRAVERMAN, S ;

MECHOULA.H .

TETRAHEDRON, 1974, 30 (21) :3883-3890

[2] ALLENYLPALLADIUM(II) SPECIES - POSSIBLE INTERMEDIATES IN THE TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0)-CATALYSED FORMATION OF ALLENES FROM PROP-2-YNYLIC SUBSTRATES [J].

ELSEVIER, CJ ;

KLEIJN, H ;

RUITENBERG, K ;

VERMEER, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (24) :1529-1530

[3] ANTI STEREOSELECTIVITY IN THE PALLADIUM(0)-CATALYZED CONVERSION OF PROPARGYLIC ESTERS INTO ALLENES BY PHENYLZINC CHLORIDE [J].

ELSEVIER, CJ ;

STEHOUWER, PM ;

WESTMIJZE, H ;

VERMEER, P .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1103-1105

[4]

HIROI K, 1983, SYNTHESIS-STUTTGART, P1040

[5] PALLADIUM-CATALYZED SYNTHESIS OF ALLENES [J].

JEFFERYLUONG, T ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1980, 21 (52) :5019-5020

[6]

MORI K, 1978, TETRAHEDRON LETT, V43, P4127

[7]

Noyori R., 1994, ASYMMETRIC CATALYSIS

[8]

OKSSON LI, 1979, ACTA CHEM SCAND, V33, P679

[9] PALLADIUM(O)-PROMOTED SYNTHESIS OF FUNCTIONALLY SUBSTITUTED ALLENES BY MEANS OF ORGANOZINC COMPOUNDS [J].

RUITENBERG, K ;

KLEIJN, H ;

ELSEVIER, CJ ;

MEIJER, J ;

VERMEER, P .

TETRAHEDRON LETTERS, 1981, 22 (15) :1451-1452

[10]

SIR CJ, 1972, J AM CHEM SOC, V94, P3643

← 1 2 →