Nanocatalysts for Rearrangement Reactions

García‐Álvarez, Joaquín; García‐Garrido, Sergio E.; Cadierno, Victorio

doi:10.1002/9781118609811.ch8

Cited by 2 publications

(1 citation statement)

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“…With that purpose and due to the large π‐acidic character of Au complexes, the selection of alkynes as benchmark substrates flourish as a wise choice based on the diverse chemical possibilities of this pair Au‐alkyne [37–41] . Interestingly, a broad number of organic transformations can be successfully accomplished such as cyclization, hydration, redox isomerization or rearrangements such as the Rupe or Meyer–Schuster ones (Scheme 1), [42–46] gold N‐heterocyclic carbenes (NHCs) playing a relevant role in the catalysis of these type of chemical processes [47–49] …”

Section: Introductionmentioning

confidence: 99%

Alcohol Dehydrogenases and N‐Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β‐Disubstituted Allylic Alcohols

2021

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The combination of gold(I) and enzyme catalysis is used in at wo-step approach, including Meyer-Schuster rearrangement of as eries of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates,toprovide optically pure b,b-disubstituted allylic alcohols.T his cascade involves ag old N-heterocyclic carbene and an enzyme,d emonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions.T he combination of [1,3bis(2,6-) and aselective alcohol dehydrogenase (ADH-A from Rhodococcus ruber,K RED-P1-A12 or KRED-P3-G09) led to the synthesis of as eries of optically active (E)-4-arylpent-3-en-2ols in good yields (65-86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives.T he use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93-> 99 %ee) for ab road panel of substrates.

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Section: Introductionmentioning

confidence: 99%