Decomposition reactions of hydroxyalkylphosphorus compounds. II. Reaction of benzylbis(.alpha.-hydroxybenzyl)phosphine oxide with benzaldehyde imines

Pepperman, Armand B.; Siddall, T. H.

doi:10.1021/jo00902a009

Cited by 4 publications

(1 citation statement)

References 12 publications

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“…The following were prepared by known literature procedures: 3-isopropyl-2-methylhex-5-en-3-ol, 10 , 3- tert -butyl-2,2-dimethylhex-5-en-3-ol, 13 , benzylidenebutylamine, 26 , benzyl(3-methylbut-2-enylidene)amine, 28 , benzylhexylideneamine, 30 , benzylcyclohexyl methyleneamine, 32 , benzyl(1-phenylethylidene)amine, 34 , crotonic acid chloride, 2,2-di( tert -butyl)oxirane, 55 , 2,2,6-trimethylhept-5-en-3-one …”

Section: Methodsmentioning

confidence: 99%

Preparation and Reactions of Masked Allylic Organozinc Reagents

Jones

Knöchel

1998

J. Org. Chem.

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Allylic zinc reagents have been prepared from sterically hindered homoallylic alcohols 10 and 13, using a novel fragmentation reaction of the corresponding zinc alkoxide, without any homocoupling products. These allylic zinc reagents react with a range of electrophiles in good to excellent yields. Substituted allylic zinc reagents have also been prepared in this manner. alpha-Substituted homoallylic alcohols 37, 46, and 51 give solely alpha-substituted products after the fragmentation-allylation sequence; these products are obtained not only regioselectively but also with extremely high anti diastereoselectivity. Likewise, gamma-substituted homoallylic alcohols 57 and 58, undergo the fragmentation-allylation reaction to give gamma-substituted products. The reaction has also been demonstrated to be catalytic in zinc salts.

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