Diisopropyl tartrate (E)-γ-(dimethylphenylsilyl)allylboronate, a chiral allylic alcohol β-carbanion equivalent for the enantioselective synthesis of 2-butene-1,4-diols from aldehydes

✍ Scribed by William R. Roush; Paul T. Grover

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 274 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97300-3

✦ Synopsis

An enantioselective synthesis of I-subs&ted (E)-2-buten-1.4~dials is akscribcd. The method involves the reaction of akiehydes with the chiral PhM$i-substituted allylboronate 3 followed by epoxiaktion (dbnethyl dioxirane) and acid catalyzed Petersen rearrangement of the intermediate epoxysilanols.

In the preceding communication we described the enantioselective synthesis of anti 1,Zdiols 3 via the reactions of aldehydes and the chiml (E!)-)c(alkoxysilyl)allylbomnate 1.1 Although this method provides anti sihtnols 2 and the derived anti diols 3 with excellent diastereoselectivity, the enantioselectivity of 1 is only moderate (6472% e.e.). We report herein the synthesis and aldehyde allylboration reactions of the analogous