Reagent control of stereochemistry in allylic additions to chiral aldehydes with CpMo(NO)(X)(2‐methallyl) complexes of high enantiomeric purity

Faller, J. W.; Nguyen, Jenna Thu; Mazzieri, María R.

doi:10.1002/aoc.590090313

Cited by 6 publications

(1 citation statement)

References 17 publications

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“…The precursors for oxygen heterocycle formation—the racemic or enantiopure enallenols 1 a and 1 b (Scheme , below) and 1 c and 1 d (Scheme , below)—were readily prepared from the appropriate starting 4‐oxoazetidine‐2‐carbaldehydes through regiocontrolled indium‐mediated Barbier‐type carbonyl–allenylation reactions in aqueous media, as we have previously described 10a. The optically active precursors syn ‐ 1 e and anti ‐ 1 e were prepared from homomethallylic alcohol 2 and aldehyde 3 10b in a four‐step sequence as shown in Scheme . Enallenol 1 f was prepared from salicylaldehyde by using our methodology 10c…”

Section: Resultsmentioning

confidence: 99%

Striking Alkenol Versus Allenol Reactivity: Metal‐Catalyzed Chemodifferentiating Oxycyclization of Enallenols

Alcaide

Almendros

Campo

et al. 2011

Chemistry A European J

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An efficient chemodivergent metal-controlled methodology for the generation of different highly functionalized oxygen heterocycles from common enallenol substrates has been developed. Chemoselectivity control in the O-C functionalization of an enallenol can be achieved through the choice of catalyst: AuCl(3), PdCl(2), and [PtCl(2)(CH(2)=CH(2))](2) exclusively afford dihydrofurans through selective activation of the allenol moiety, whereas FeCl(3) solely gives tetrahydrofurans or tetrahydropyrans through selective activation of the alkenol moiety. We have also shown that a combination of metal-mediated hydroalkoxylation and allenic aminocyclization reactions can lead to a useful preparation of the tetrahydrofuro[3,2-b]piperidine core of the antimalarial alkaloid isofebrifugine. These divergent heterocyclization reactions have been developed experimentally and additionally, their mechanisms have been investigated by a theoretical study.

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Section: Resultsmentioning

confidence: 99%