The Journal of Organic Chemistry

A stereospecific synthesis of hydroxyl-differentiated (E)-and (Z)-1, 4-enediols

RB Miller, MI Al-Hassan

Index: Miller, R. Bryan; Al-Hassan, Mohammed I. Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4113 - 4116

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Citation Number: 18

Abstract

1 Et H 78 80 1 Me Me 77 54 1 Ph H 69 70 1(-CH2-) 5 80 51 2 Et H 75 81 2 Me Me 75 70 tetrahydrofuran to diisobutylaluminum hydride was employed in the hydroalumination step in order to preferentially coordinate the aluminum by the tetrahydrofuranyl oxygen in analogy to a recent observation by ZweifeL4 Under these conditions, no cleavage of the tetrahydropyranyl ether was observed, but unfortunately the yield of the desired product 1 ...