SYNTHESIS OF AXIALLY DISSYMMETRIC 3,5-OCTADIENE FRAMEWORK WITH C2 CHIRALITY VIA PALLADIUM(II)-CATALYZED TWOFOLD SIGMATROPIC REARRANGEMENT

DOI: 10.1016/S0040-4039(00)86676-9

Source and publish data:

Tetrahedron Letters p. 1157 - 1160 (1988)

Update date:2022-08-05

Topics:

Authors:

Saito, Seiki

Hamano, Shin-ichi

Moriyama, Hiroshi

Okada, Keiji

Moriwake, Toshio

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Article abstract of DOI:10.1016/S0040-4039(00)86676-9

Palladium(II)-catalyzed <3,3>sigmatropic rearrangement of (4R,5R)-4,5-(bisacetoxy)-1,8-(bisbenzyloxy)-2(E),6(E)-octadiene has proceeded convergently to give (2S,7S)-2,7-(bisacetoxy)-1,8-(bisbenzyloxy)-3(E),5(E)-octadiene, translating the original chirality completely to the migration termini, which constitutes a novel synthesis of optically pure 3,5-octadiene with C₂ chirality.

Full text of DOI:10.1016/S0040-4039(00)86676-9

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