Journal
TETRAHEDRON LETTERS
Volume 73, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153098
Keywords
Ring contraction; Lactam; Nucleophilic addition; Pyrrolidine; Grignard reagent
Categories
Funding
- JSPS KAKENHI [JP19K05467, JP18K06590, JP19K23815]
- Hoansha Foundation
- Mitsubishi Tanabe Pharma Award in Synthetic Organic Chemistry, Japan
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A new method for synthesizing 2-acyl pyrrolidines has been developed through sequential nucleophilic addition/ring contraction of alpha-bromo N-iminolactam with organometallic reagents. This reaction allows the incorporation of various groups, including aryl, heteroaryl, alkenyl, alkynyl, and alkyl groups, into the facial construction of 2-acyl pyrrolidines. Moreover, the 2-acyl pyrrolidine products can be further transformed into different compounds such as pyrrolidinyl alcohol, epoxide, b-lactam, and pyrazole.
A sequential nucleophilic addition/ring contraction of alpha-bromo N-iminolactam with organometallic reagents for the synthesis of 2-acyl pyrrolidines has been developed. The reaction allows facial construction of 2-acyl pyrrolidines incorporating not only aryl and heteroaryl groups, but alkenyl, alkynyl, and alkyl groups. Moreover, 2-acyl pyrrolidine products can be further transformed into the pyrrolidinyl alcohol, epoxide, b-lactam, and pyrazole. (C) 2021 Elsevier Ltd. All rights reserved.
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