Synthesis of Chiral α-Vinyl Quaternary α-Amino Acid Derivatives through Organocatalyzed Asymmetric Conjugate Addition of Azlactone to Ynone

Abstract The first successful example of the stereoselective conjugate addition of azlactones to ynones is reported. Diaminomethylenemalononitrile organocatalysts efficiently promoted the asymmetric conjugate addition of azlactones to ynones, affording the corresponding α-vinyl quaternary α-amino acid derivatives in high yields with good to high enantioselectivities (up to 91% ee).

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-07
DOI
https://doi.org/10.1021/acs.joc.6c01579
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
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article

Synthesis of Chiral α-Vinyl Quaternary α-Amino Acid Derivatives through Organocatalyzed Asymmetric Conjugate Addition of Azlactone to Ynone

Yuta Iino, Kosuke Nakashima, Tsuyoshi Miura, Shin‐ichi Hirashima et al.
The Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
article

Synthesis of Chiral α-Vinyl Quaternary α-Amino Acid Derivatives through Organocatalyzed Asymmetric Conjugate Addition of Azlactone to Ynone

Yuta Iino, Kosuke Nakashima, Tsuyoshi Miura, Shin‐ichi Hirashima, Yasuyuki Matsushima
article en

Abstract

Abstract The first successful example of the stereoselective conjugate addition of azlactones to ynones is reported. Diaminomethylenemalononitrile organocatalysts efficiently promoted the asymmetric conjugate addition of azlactones to ynones, affording the corresponding α-vinyl quaternary α-amino acid derivatives in high yields with good to high enantioselectivities (up to 91% ee).

The Journal of Organic Chemistry
Tokyo University of Pharmacy and Life Sciences (JP)
Openalex Percentile: Top 24%
Asymmetric Synthesis and Catalysis
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