Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

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Abstract: An enantiodivergent method for the synthesis of multiply substituted allenes is described. Highly enantioenriched, point‐chiral boronic esters were synthesized by homologation of α‐seleno alkenyl boronic esters with lithiated carbamates and eliminated to form axially chiral allene products. By employing either oxidative or alkylative conditions, both syn and anti elimination could be achieved with complete stereospecificity. The process enables the synthesis of either M or P allenes from a single isomer of a point‐chiral precursor and can be employed for the enantioselective assembly of di‐, tri‐, and tetrasubstituted allenes.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer ; volume:57 ; number:27 ; year:2018 ; pages:8203-8208 ; extent:6
Angewandte Chemie / International edition. International edition ; 57, Heft 27 (2018), 8203-8208 (gesamt 6)

Creator: Armstrong, Roly J.
Nandakumar, Meganathan
Dias, Rafael M. P.
Noble, Adam
Myers, Eddie L.
Aggarwal, Varinder K.

DOI: 10.1002/anie.201804446

URN: urn:nbn:de:101:1-2022081809160225535017

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Associated

Armstrong, Roly J.
Nandakumar, Meganathan
Dias, Rafael M. P.
Noble, Adam
Myers, Eddie L.
Aggarwal, Varinder K.

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Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

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