Synthesis and diastereoselective complexation of enantiopure sulfinyl dienes: The preparation of sulfinyl iron(0) dienes

被引：58

作者：

Paley, RS ^{[1
]}

deDios, A ^{[1
]}

Estroff, LA ^{[1
]}

Lafontaine, JA ^{[1
]}

Montero, C ^{[1
]}

McCulley, DJ ^{[1
]}

Rubio, MB ^{[1
]}

Ventura, MP ^{[1
]}

Weers, HL ^{[1
]}

delaPradilla, RF ^{[1
]}

Castro, S ^{[1
]}

Dorado, R ^{[1
]}

Morente, M ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,E-28006 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 18期

关键词：

D O I：

10.1021/jo970693a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of a diverse array of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via Stille coupling of halovinyl sulfoxides and vinyl stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of the corresponding sulfinyl diene iron(0) tricarbonyl complexes was accomplished by utilizing Fe(CO)(5)/NMO or (bda)Fe(CO)(3) as iron(0) tricarbonyl transfer reagents. Installation of the iron(0) tricarbonyl fragment was shown to be highly diastereoselective (10-16:1) for (R)-(1Z)-1-sulfinyl dienes, most likely as a result of allylic 1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene is also described.

引用

页码：6326 / 6343

页数：18

共 91 条

[1] PREPARATION OF TRICARBONYL(ETA-4-VINYLKETENE)IRON(0) COMPLEXES FROM TRICARBONYL(ETA-4-VINYL KETONE)IRON(0) COMPLEXES AND THEIR SUBSEQUENT CONVERSION TO TRICARBONYL(ETA-4-VINYLKETENIMINE)IRON(0) COMPLEXES [J].