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1.
Angew Chem Int Ed Engl ; 58(31): 10718-10722, 2019 07 29.
Artigo em Inglês | MEDLINE | ID: mdl-31166641

RESUMO

The 20-membered marine macrodiolide clavosolide A is prepared in 7 steps (LLS) in the absence of protecting groups or chiral auxiliaries via enantioselective alcohol-mediated carbonyl addition. In 9 prior total syntheses, 11-34 steps (LLS) were required.


Assuntos
Álcoois/química , Compostos Alílicos/síntese química , Macrolídeos/síntese química , Policetídeos/química , Compostos Alílicos/química , Macrolídeos/química , Estrutura Molecular , Estereoisomerismo
2.
J Am Chem Soc ; 140(30): 9392-9395, 2018 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-30020777

RESUMO

Enantioselectivity increases with increasing carbonyl electrophilicity in 2-propanol-mediated reductive couplings of aldehydes with branched aryl-substituted allylic acetates to form products of carbonyl anti-(α-aryl)allylation. This unusual phenomenon is caused by aldehyde coordination to diastereomeric kinetic vs thermodynamic carbonyl binding sites that deliver enantiomeric products. Exploiting this effect, anti-diastereo- and enantioselective (α-aryl)allylations of fluoral hydrate and difluoroacetaldehyde ethyl hemiacetal were developed.


Assuntos
Acetaldeído/análogos & derivados , Acetais/síntese química , Compostos Alílicos/síntese química , Derivados da Atropina/síntese química , Irídio/química , 2-Propanol/química , Acetaldeído/química , Acetatos/química , Catálise , Cinética , Oxirredução , Estereoisomerismo , Termodinâmica
3.
Angew Chem Int Ed Engl ; 57(5): 1390-1393, 2018 01 26.
Artigo em Inglês | MEDLINE | ID: mdl-29240280

RESUMO

An inside job: Enantioselective phthalide synthesis was achieved through internal redox allylation of o-phthalaldehydes. Oxidative esterification is balanced by reductive carbonyl addition to achieve an overall redox-neutral process. This method enabled formal syntheses of ent-spirolaxine methyl ether and CJ-12,954.


Assuntos
Benzofuranos/química , Irídio/química , o-Ftalaldeído/química , Catálise , Esterificação , Hidrogenação , Oxirredução , Estereoisomerismo
4.
Tetrahedron Asymmetry ; 73(26): 3643-3651, 2017 Jun 29.
Artigo em Inglês | MEDLINE | ID: mdl-31827315

RESUMO

Several Gold's reagents were synthesized from cyanuric chloride and N,N-dialkylformamides. These synthetic equivalents of N,N-dimethylformamide dimethyl acetal were used in an optimized and scalable procedure for the regioselective synthesis of a variety of enaminones from ketone starting materials, whose utility was demonstrated by the stereoselective synthesis of Rawal-type dienes.

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