Enantioselective Synthesis of Pyrrolidines by a Phosphine-Catalyzed γ-Umpolung/β-Umpolung Cascade.

Autor:	Maddigan-Wyatt JT; School of Chemistry, Monash University, Clayton, Victoria 3800, Australia., Cao J; School of Chemistry, Monash University, Clayton, Victoria 3800, Australia., Ametovski J; School of Chemistry, Monash University, Clayton, Victoria 3800, Australia., Hooper JF; School of Chemistry, Monash University, Clayton, Victoria 3800, Australia., Lupton DW; School of Chemistry, Monash University, Clayton, Victoria 3800, Australia.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2022 Apr 22; Vol. 24 (15), pp. 2847-2852. Date of Electronic Publication: 2022 Apr 11.
DOI:	10.1021/acs.orglett.2c00785
Abstrakt:	Herein, we report an enantioselective catalytic annulation of electron-poor allenes with aminocrotonates. The reaction proceeds by the umpolung γ-amination of the allenoate and β-umpolung intramolecular conjugate addition. The reaction provides ready access to pyrrolidines using a homochiral phosphepine catalyst, which allows most products to form in good yields (55-85%) with ≥95:5 er and ≥4:1 dr. An assisted tandem-catalytic variant is also viable, and mechanistic studies supporting the proposed reaction pathway are reported.
Databáze:	MEDLINE
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