Journal ArticleDOI
Highly Diastereoselective and Enantiospecific Allylation of Ketones and Imines Using Borinic Esters: Contiguous Quaternary Stereogenic Centers
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TLDR
3,3-Disubstituted allylic boronic esters can be converted into the corresponding borinic esters by the sequential addition of nBuLi and TFAA, which allows the highly selective allylation of both ketones and ketimines, and facile access to adjacent quaternary stereocenters with full stereocontrol.Abstract:
3,3-Disubstituted allylic boronic esters are not sufficiently reactive to react with ketones and imines. However, they can be converted into the corresponding borinic esters by the sequential addition of nBuLi and TFAA. These reactive intermediates possess the perfect balance between reactivity and configurational stability. Their enhanced reactivity allows the highly selective allylation of both ketones and ketimines, and facile access to adjacent quaternary stereocenters with full stereocontrol. The versatility of the methodology is demonstrated in the construction of all possible stereoisomers of a quaternary-quaternary motif and by the allylation of the heterocycles, dihydroisoquinoline and indole.read more
Citations
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Journal ArticleDOI
Recent Advances in the Preparation and Application of Allylboron Species in Organic Synthesis
Colin Diner,Kálmán J. Szabó +1 more
TL;DR: In this Perspective, the most important recent breakthroughs in selective allylboron chemistry (both the synthesis and application of these species) are highlighted and an outlook toward the future is provided.
Journal ArticleDOI
All-carbon quaternary centers in natural products and medicinal chemistry: recent advances
Taotao Ling,Fatima Rivas +1 more
Journal ArticleDOI
Nonracemic allylic boronates through enantiotopic-group-selective cross-coupling of geminal bis(boronates) and vinyl halides.
TL;DR: Mechanical experiments suggest the operation of a pathway involving outer-sphere stereoinvertive transmetalation in 1,1-bis(pinacolboronate) esters to generate nonracemic allyl boronates with high levels of enantioselectivity.
Journal ArticleDOI
Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes
TL;DR: A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials.
Journal ArticleDOI
Catalytic Asymmetric Umpolung Allylation of Imines.
TL;DR: An iridium-catalyzed asymmetric umpolung allylation of imines is reported as a general approach to prepare 1,4-disubstituted homoallylic amines, a fundamental class of compounds that are hitherto not straightforward to obtain.
References
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Journal ArticleDOI
Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and Ketones
Scott E. Denmark,Jiping Fu +1 more
BookDOI
Boronic acids : preparation and applications in organic synthesis and medicine
TL;DR: In this article, the authors present a list of Boronic acid derivatives and their application in the following: 1.1 Introduction. 2.2 Borylation of Aromatic Halides and Trif lates.
Journal ArticleDOI
Catalytic enantioselective construction of all-carbon quaternary stereocenters
Barry M. Trost,Chunhui Jiang +1 more
TL;DR: In this paper, a comprehensive account of the currently available methods of the above transformation that afford high enantioselectivities and synthetically useful yields is given. But this review is limited to all-carbon quaternary stereocenters, i.e. carbon atoms bearing four different carbon substituents.
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Recent Advances in the Preparation and Application of Allylboron Species in Organic Synthesis
Colin Diner,Kálmán J. Szabó +1 more