Tetrahedron letters

Synthesis of axially dissymmetric 3, 5-octadiene framework with C 2 chirality via palladium (II)-catalyzed twofold [3, 3] sigmatropic rearrangement

…, S Hamano, H Moriyama, K Okada, T Moriwake

Index: Saito, Seiki; Hamano, Shin-ichi; Moriyama, Hiroshi; Okada, Keiji; Moriwake, Toshio Tetrahedron Letters, 1988 , vol. 29, # 10 p. 1157 - 1160

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Citation Number: 20

Abstract

Abstract Palladium (Il)-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 C 2 chirality.

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