Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of N‑Alkoxylactams

Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of N‑Alkoxylactams

A nucleophilic addition/ring-contractive rearrangement of α-bromo N-alkoxylactams with organometallic reagents was developed, providing an efficient access to α-acylpyrrolidines incorporating various C­(sp 2) units such as aryl, heteroaryl, and alkenyl groups. The sequential reaction proceeds throug...

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Veröffentlicht in:Organic letters 2020-12, Vol.22 (24), p.9740-9744
Hauptverfasser: Takeda, Norihiko, Kobori, Yukiko, Okamura, Kohei, Yasui, Motohiro, Ueda, Masafumi
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container_end_page 9744
container_issue 24
container_start_page 9740
container_title Organic letters
container_volume 22
creator Takeda, Norihiko
Kobori, Yukiko
Okamura, Kohei
Yasui, Motohiro
Ueda, Masafumi
description A nucleophilic addition/ring-contractive rearrangement of α-bromo N-alkoxylactams with organometallic reagents was developed, providing an efficient access to α-acylpyrrolidines incorporating various C­(sp 2) units such as aryl, heteroaryl, and alkenyl groups. The sequential reaction proceeds through a five-membered chelate formation using nucleophilic addition followed by ring contraction via the formation of N,O-hemiaminal with good yields and a broad substrate scope. Moreover, a preliminary result with the use of the chiral N-alkoxylactam for the diastereoselective reaction is described.
doi_str_mv 10.1021/acs.orglett.0c03821
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title Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of N‑Alkoxylactams
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