Regio‐ and Stereoselective Homologation of 1,2‐Bis (Boronic Esters): Stereocontrolled Synthesis of 1,3‐Diols and Sch 725674
Abstract: 1,2‐Bis (boronic esters), derived from the enantioselective diboration of terminal alkenes, can be selectively homologated at the primary boronic ester by using enantioenriched primary/secondary lithiated carbamates or benzoates to give 1,3‐bis (boronic esters), which can be subsequently oxidized to the corresponding secondary‐secondary and secondary‐tertiary 1,3‐diols with full stereocontrol. The transformation was applied to a concise total synthesis of the 14‐membered macrolactone, Sch 725674. The nine‐step synthetic route also features a novel desymmetrizing enantioselective diboration of a divinyl carbinol derivative and high‐yielding late‐stage cross‐metathesis and Yamaguchi macrolactonization reactions.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Regio‐ and Stereoselective Homologation of 1,2‐Bis (Boronic Esters): Stereocontrolled Synthesis of 1,3‐Diols and Sch 725674 ; volume:128 ; number:47 ; year:2016 ; pages:14883-14887 ; extent:5
Angewandte Chemie ; 128, Heft 47 (2016), 14883-14887 (gesamt 5)
- Urheber
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Fawcett, Alexander
Nitsch, Dominik
Ali, Muhammad
Bateman, Joseph M.
Myers, Eddie L.
Aggarwal, Varinder K.
- DOI
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10.1002/ange.201608406
- URN
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urn:nbn:de:101:1-2022103104560240064507
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:35 MESZ
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Beteiligte
- Fawcett, Alexander
- Nitsch, Dominik
- Ali, Muhammad
- Bateman, Joseph M.
- Myers, Eddie L.
- Aggarwal, Varinder K.
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