Development of the Efficient Asymmetric Synthesis Utilizing Characteristic of Chiral Auxiliary
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- Ozeki Minoru
- Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University
Bibliographic Information
- Other Title
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- 不斉補助基の特性を活かした効率的不斉合成法の開発
- フセイ ホジョキ ノ トクセイ オ イカシタ コウリツテキ フセイ ゴウセイホウ ノ カイハツ
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Abstract
In this article, we describe asymmetric syntheses taking advantage of chiral auxiliary characteristics. In the asymmetric Michael addition reaction of chiral thiol, we developed a novel tandem Michael-MPV (Meerwein-Ponndorf-Verley) reaction, which provided the 1,3-mercaptoalcohols with two or three chiral centers. Moreover, multi-contiguous chiral centers were finely constructed in one pot utilizing three types of Michael addition-initiated reactions, i.e., tandem Michael-aldol reaction, double Michael addition reaction, double Michael-aldol reaction, which were triggered by a nucleophilic attack of a novel recyclable chiral amine. Asymmetric syntheses of a number of biologically active compounds such as captopril, γ-lactone natural products, (+)-negamycin and β-lactam were achieved as an application of our reactions.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 68 (8), 854-865, 2010
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001205311748096
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- NII Article ID
- 10026870461
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- NII Book ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC3cXhtVKkt7rK
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 10802858
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed