Enantioselective syntheses of homopropargylic alcohols via asymmetric allenylboration
Organic letters, 2018•ACS Publications
… In connection with an ongoing problem in natural product synthesis, we became interested
in asymmetric propargylation with 1-substituted allenylboronate reagents (1 in Scheme 1).
We envisioned that enantioenriched homopropargylic alcohols 2 should be accessible from
the addition of boronates 1 to aldehydes through the proper control of enantioselectivity by a
suitable chiral catalyst. Inspired by the work of Antilla (10a) and Reddy (10b) on chiral,
nonracemic phosphoric acid catalyzed … In summary, we developed a chiral phosphoric acid …
in asymmetric propargylation with 1-substituted allenylboronate reagents (1 in Scheme 1).
We envisioned that enantioenriched homopropargylic alcohols 2 should be accessible from
the addition of boronates 1 to aldehydes through the proper control of enantioselectivity by a
suitable chiral catalyst. Inspired by the work of Antilla (10a) and Reddy (10b) on chiral,
nonracemic phosphoric acid catalyzed … In summary, we developed a chiral phosphoric acid …
A chiral phosphoric acid catalyzed allenylboration reaction is reported. Homopropargyl alcohols with an internal alkyne unit were obtained in good yields with high enantioselectivities under the developed conditions.
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