88088-52-2Relevant articles and documents
-WITTIG SIGMATROPIC REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM; AN EMERGING TOOL FOR CONTROL OF ACYCLIC STEREOCHEMISTRY
Mikami, Koichi,Azuma, Ken-Ichi,Nakai, Takeshi
, p. 2303 - 2308 (2007/10/02)
The -Wittig rearrangement of properly designated (E)- and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo- and erythro-selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds.Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (+/-)-oudemansin.Further, the high level of diastereoselection is maintained in the reaction of the α-methylcrotyl counterparts, together with the exclusive formation of the (E)-olefinic bond.
ENHANCEMENT OF ERYTHRO-SELECTIVITY IN THE -WITTIG REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM AND ITS USE IN THE STEREOCONTROLLED FORMAL SYNTHESIS OF (+/-)-OUDEMANSIN
Mikami, Koichi,Azuma, Ken-ichi,Nakai, Takeshi
, p. 1379 - 1382 (2007/10/02)
The -Wittig variant of (Z)-crotyl ether involving trimethylsilylethynyl (or 1-propynyl) group as the key substituent on the carbanion terminus exhibits an exceptionally high level of erythro-selection, and its synthetic potential is illustrated in th