Enantioselective Allenylation of Aldehydes via Brønsted Acid Catalysis

Mengzhou Wang; Shahriar Khan; Evangelos Miliordos; Ming Chen

doi:10.1002/adsc.201801080

Enantioselective Allenylation of Aldehydes via Brønsted Acid Catalysis

Mengzhou Wang, Shahriar Khan, Evangelos Miliordos, Ming Chen

Advanced Computing for Chemistry and Mat

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50 Scopus citations

Abstract

An enantioselective allenylation of aldehydes catalyzed by a chiral, nonracemic phosphoric acid was reported. Under the developed conditions, 1,1′-disubstituted allenic alcohols were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was supported by experimental data. (Figure presented.).

Original language	English
Pages (from-to)	4634-4639
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	23
DOIs	https://doi.org/10.1002/adsc.201801080
State	Published - Dec 3 2018

Funding

Financial support provided by Auburn University is gratefully acknowledged. We thank the Schneller, Merner and Gordon groups at Auburn University for sharing the chemicals.

Keywords

Allenic alcohols
Asymmetric allenylation
Phosphoric acid

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10.1002/adsc.201801080

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title = "Enantioselective Allenylation of Aldehydes via Br{\o}nsted Acid Catalysis",

abstract = "An enantioselective allenylation of aldehydes catalyzed by a chiral, nonracemic phosphoric acid was reported. Under the developed conditions, 1,1′-disubstituted allenic alcohols were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was supported by experimental data. (Figure presented.).",

keywords = "Allenic alcohols, Asymmetric allenylation, Phosphoric acid",

author = "Mengzhou Wang and Shahriar Khan and Evangelos Miliordos and Ming Chen",

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AU - Wang, Mengzhou

AU - Khan, Shahriar

AU - Miliordos, Evangelos

AU - Chen, Ming

PY - 2018/12/3

Y1 - 2018/12/3

N2 - An enantioselective allenylation of aldehydes catalyzed by a chiral, nonracemic phosphoric acid was reported. Under the developed conditions, 1,1′-disubstituted allenic alcohols were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was supported by experimental data. (Figure presented.).

AB - An enantioselective allenylation of aldehydes catalyzed by a chiral, nonracemic phosphoric acid was reported. Under the developed conditions, 1,1′-disubstituted allenic alcohols were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was supported by experimental data. (Figure presented.).

KW - Allenic alcohols

KW - Asymmetric allenylation

KW - Phosphoric acid

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U2 - 10.1002/adsc.201801080

DO - 10.1002/adsc.201801080

M3 - Article

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VL - 360

SP - 4634

EP - 4639

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 23

ER -

Enantioselective Allenylation of Aldehydes via Brønsted Acid Catalysis

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