Synthesis of Highly Congested Tertiary Alcohols via the [3,3] Radical Deconstruction of Breslow Intermediates.
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DOI: 10.1021/acs.orglett.2c01627
Abstract: Pericyclic processes such as [3,3]-sigmatropic rearrangements leading to the rapid generation of molecular complexity constitute highly valuable tools in organic synthesis. Herein, we report the formation of particularly hindered tertiary alcohols via rearrangement of Breslow… read more here.
Keywords: synthesis highly; breslow intermediates; highly congested; alcohols via ... See more keywords
Dehydroxylative Arylation of Alcohols via Paired Electrolysis.
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DOI: 10.1021/acs.orglett.2c03136
Abstract: Nonactivated alcohols along with arene compounds are used in electrochemical dehydroxylative arylation for constructing C(sp3)-C(sp2) bonds. The PIII reagent undergoes single-electron anodic oxidation to form its radical cation, which reacts with the alcohol to produce… read more here.
Keywords: via paired; alcohols via; dehydroxylative arylation; paired electrolysis ... See more keywords
Access to 1,2- and 1,3-Amino Alcohols via Cu-Catalyzed Enantioselective Borylations of Allylamines.
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DOI: 10.1021/acs.orglett.4c03170
Abstract: We report Cu-catalyzed enantioselective borylation/oxidation sequences that afford either enantioenriched 1,2- or 1,3-amino alcohols starting from N,N-protected allylamines as a common platform. The approach is based on the mechanistic specificities of catalytic hydroboration and protoboration… read more here.
Keywords: catalyzed enantioselective; alcohols via; amino alcohols; amino ... See more keywords
Direct Synthesis of Amides from Nitro Compounds and Alcohols via Borrowing Hydrogenation∇.
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DOI: 10.1021/acs.orglett.5c00600
Abstract: Herein, we report a RuH2(CO)(PPh3)3 catalyzed direct amidation of alcohols using readily available nitro compounds via a catalytic borrowing hydrogen method. This reaction proceeded via cascade reactions, including oxidation of alcohol, reduction of nitro group… read more here.
Keywords: direct synthesis; nitro compounds; alcohols via; compounds alcohols ... See more keywords
O-Allylhydroxyamine: A Bifunctional Olefin for Construction of Axially and Centrally Chiral Amino Alcohols via Asymmetric Carboamidation.
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.3c01162
Abstract: Difunctionalization of olefins offers an attractive approach to access complex chiral structures. Reported herein is the design of N-protected O-allylhydroxyamines as bifunctional olefins that undergo catalytic asymmetric 1,2-carboamidation with three classes of (hetero)arenes to afford… read more here.
Keywords: asymmetric carboamidation; chiral amino; alcohols via; amino ... See more keywords
Divergent reactions of oxindoles with amino alcohols via the borrowing hydrogen process: oxindole ring opening vs. C3 alkylation
Sign Up to like & getrecommendations! Published in 2018 at "Organic chemistry frontiers"
DOI: 10.1039/c8qo00184g
Abstract: Oxindoles display a diverse pattern of reactivity upon reaction with different classes of amino alcohols via the borrowing hydrogen process. Whereas the reaction with N-acetyl amino alcohols leads to C3 alkylation, the reaction with N-alkyl… read more here.
Keywords: via borrowing; borrowing hydrogen; amino alcohols; reaction ... See more keywords