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.
Highlights
An enantiodivergent method for the synthesis of multiply substituted allenes is described
Point-chiral boronic esters were synthesized by homologation of a-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
Summary
An enantiodivergent method for the synthesis of multiply substituted allenes is described. Upon treatment of a THF solution of boronic ester 3 with m-CPBA at À45 8C, we obtained the desired allene product (P)-4 in 41 % yield along with alcohol 5 in 41 % yield, which results from competing oxidation of the CÀB bond (Table 1, entry 1).
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