Concise and Highly Stereoselective Synthesis of <i>β</i>,<i>β</i>-Disubstituted <i>α</i>,<i>β</i>-Unsaturated Esters
Building on our previously reported techniques, we developed a concise and highly stereoselective synthesis method for β,β-disubstituted α,β-unsaturated esters. This synthesis comprises 3 reactions: the aldol reaction of acetic ester derivatives with ketones, the acetylation of tert-alcohols, and an elimination reaction utilizing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). During the acetylation process, acetic anhydride and 4-dimethylaminopyridine (DMAP) facilitated the smooth acetylation of bulky tert-alcohols; however, employing DBU as a base reduced the yields. Additionally, the removal of excess DMAP effectively suppressed the formation of unwanted byproducts during the elimination step.
Authors
- Hirotaka Sasa
- Naoto Kojima (ORCID: https://orcid.org/0000-0002-4544-4583)
- Takashi Shigeta (ORCID: https://orcid.org/0000-0003-2212-5085)
- Satoshi Yamanouchi (ORCID: https://orcid.org/0000-0001-8986-8647)
- Masaru Yamakawa
- Minoru Ozeki
- Kazumasa Fukuda (ORCID: https://orcid.org/0000-0001-6126-6118)
- M Tsuda
- Aya Niki
- Kenji Arimitsu (ORCID: https://orcid.org/0000-0003-2844-1652)
- Takuya Matsumoto (ORCID: https://orcid.org/0000-0003-4689-5770)
- Shinzo Hosoi
- Hiroki IWASAKI
- Tetsuya Kajimoto (ORCID: https://orcid.org/0000-0002-5738-3503)
- Ikuo Kawasaki
- Maaya Nobata
Institutions
- Mukogawa Women's University (JP)
- Ritsumeikan University (JP)
- University of Shizuoka (JP)
- Osaka Ohtani University (JP)
- Nagasaki International University (JP)
- Kyoto Pharmaceutical University (JP)
Publication Details
- Journal
- Chemical and Pharmaceutical Bulletin
- Published
- 2025-03-28
- DOI
- https://doi.org/10.1248/cpb.c24-00751
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00