Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol

被引：7
|
作者：
Meyer, Cole C. [1 ]
Dubey, Zachary J. [1 ]
Krische, Michael J. [1 ]
机构：
[1] Univ Texas Austin, Dept Chem, 105 E 24th St,A5300, Austin, TX 78712 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 14期
关键词：
Allylation; Bioisostere; Diene; Enantioselective; Iridium; CHIRAL TERTIARY ALCOHOLS; ORGANOMETALLIC REAGENTS; ASYMMETRIC CATALYSIS; CARBONYL-COMPOUNDS; ALDOL REACTION; KETONES; PROPARGYLATION; CROTYLATION; HYDROHYDROXYALKYLATION; ALLENYLATION;
D O I：
10.1002/anie.202115959
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cyclometallated iridium-PhanePhos complexes generated in situ from [Ir(cod)Cl](2) and (R)-PhanePhos catalyze 2-propanol-mediated reductive couplings of 2-substituted dienes with oxetanone and N-acyl-azetidinones to form branched homoallylic oxetanols and azetidinols with excellent control of regio- and enantioselectivity without C-C cleavage of the strained ring via enantiotopic pi-facial selection of transient allyliridium nucleophiles. This work represents the first systematic study of enantioselective additions to symmetric ketones.
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页数：5
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