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Low-valent titanium reductive elimination: a direct and highly stereoselective synthesis of vitamin a aldehyde

✍ Scribed by Guy Solladié; Valérie Berl

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
191 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

It was shown that the low-valent titanium reductive elimination could be carried out in p Rsence of a thioacetal group. An application to the synthesis of vitamin A aldkhyde is described

Low valent titanium, readily available by reduction of titanium trichloride with lithium @minium hydride, was shown to be a werful p" synthetic agent allowing the fotmation of a diene by reductive elimination of an allylic diol . We have described already a highly stexeoselective synthesis of the E, E-1,3diene central unit of vitamin A and 134s retin fmm the corresponding allylic dial. "Ti(0)" 9 CH20TBDMS -OTBDMS LiAlH, TiCI3

The reaction mechanism involves, at least in the first step, a one electron transfer from the titanium Surface.

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