β-Silyloxy Allylboronate Esters through an Aldehyde Borylation/Homologation Sequence.
Sign Up to like & getrecommendations! Published in 2020 at "Tetrahedron letters"
DOI: 10.1016/j.tetlet.2020.152082
Abstract: The areas of carbonyl borylation and the homologation of carbon-boron bonds have provided a number of fruitful methods in organic synthesis. Combining these approaches, the homologation of α-oxyboronate esters, provides pathways to access complex organoboronate… read more here.
Keywords: borylation homologation; homologation; allylboronate esters; esters aldehyde ... See more keywords
Matteson Homologation-Based Total Synthesis of Lagunamide A.
Sign Up to like & getrecommendations! Published in 2018 at "Organic letters"
DOI: 10.1021/acs.orglett.8b00576
Abstract: Matteson homologation was found to be an excellent tool for the synthesis of the polyketide fragment of lagunamide A. Starting from a chiral boronic ester, a central building block containing all stereogenic centers of the… read more here.
Keywords: based total; matteson homologation; homologation; homologation based ... See more keywords
Pd-Catalyzed Organometallic-Free Homologation of Arylboronic Acids Enabled by Chemoselective Transmetalation
Sign Up to like & getrecommendations! Published in 2023 at "ACS Catalysis"
DOI: 10.1021/acscatal.3c00921
Abstract: A Pd-catalyzed homologation of arylboronic acids is reported. Halomethylboronic acid pinacol esters (Bpin) undergo a remarkably facile, yet rare, oxidative addition enabled by an α-boryl effect. Simultaneous chemoselective transmetalation allows use of these metalloid reagents… read more here.
Keywords: chemoselective transmetalation; catalyzed organometallic; homologation arylboronic; arylboronic acids ... See more keywords
Stereocontrolled Total Synthesis of Bastimolide B Using Iterative Homologation of Boronic Esters
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c03192
Abstract: Bastimolide B is a polyhydroxy macrolide isolated from marine cyanobacteria displaying antimalarial activity. It features a dense array of hydroxylated stereogenic centers with 1,5-relationships along a hydrocarbon chain. These 1,5-polyols represent a particularly challenging motif… read more here.
Keywords: synthesis bastimolide; synthesis; bastimolide using; stereocontrolled total ... See more keywords
Nickel-catalysed carbonylative homologation of aryl iodides
Sign Up to like & getrecommendations! Published in 2018 at "Communications Chemistry"
DOI: 10.1038/s42004-018-0091-2
Abstract: Homologation is an important organic transformation which extends the carbon chain of a parent molecule, and many procedures have been established. However, although carbonylation reactions are now well developed as valuable methods for the synthesis… read more here.
Keywords: carbonylative homologation; nickel catalysed; aryl iodides; homologation ... See more keywords
Homologation of halostannanes with carbenoids: a convenient and straightforward one-step access to α-functionalized organotin reagents.
Sign Up to like & getrecommendations! Published in 2018 at "Chemical communications"
DOI: 10.1039/c8cc04786c
Abstract: A direct, single synthetic homologative transformation of halostannanes into mono- or di-substituted methyl analogues is documented. Critical for the success of the operation is the excellent nucleophilicity of carbenoid-like methyllithium reagents (LiCHXY, X, Y =… read more here.
Keywords: straightforward one; homologation halostannanes; carbenoids convenient; homologation ... See more keywords
Cooperative strategies for CO homologation.
Sign Up to like & getrecommendations! Published in 2020 at "Dalton transactions"
DOI: 10.1039/d0dt01564d
Abstract: Recent approaches in which at least two metal or main-group centres are involved in the homologation of CO are reviewed. We have characterised the strategies into three broad areas: (i) the reductive homologation of atmospheric… read more here.
Keywords: strategies homologation; metal; reductive homologation; cooperative strategies ... See more keywords
Carbenoid-Mediated Homologation Tactics for Assembling (Fluorinated) Epoxides and Aziridines
Sign Up to like & getrecommendations! Published in 2020 at "Synlett"
DOI: 10.1055/s-0040-1706404
Abstract: Homologation strategies provide highly versatile tools in organic synthesis for the introduction of a CH2 group into a given carbon skeleton. The operation can result in diverse structural motifs by tuning of the reaction conditions… read more here.
Keywords: tactics assembling; mediated homologation; homologation tactics; carbenoid mediated ... See more keywords