Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes

被引：9

作者：

Nicholson, Kieran ^{[1
]}

Peng, Yuxuan ^{[1
]}

Llopis, Natalia ^{[1
]}

Willcox, Dominic R. ^{[1
]}

Nichol, Gary S. ^{[1
]}

Langer, Thomas ^{[2
]}

Baeza, Alejandro ^{[3
,4
]}

Thomas, Stephen P. ^{[1
]}

机构：

[1] Univ Edinburgh, EaStCHEM Sch Chem, Edinburgh EH9 3FJ, Scotland

[2] AstraZeneca, Pharmaceut Technol & Dev Chem Dev UK, Macclesfield SK10 2NA, England

[3] Univ Alicante, Inst Sintesis Organ, Alicante 03080, Spain

[4] Univ Alicante, Dept Quim Organ, Alicante 03080, Spain

来源：

ACS CATALYSIS | 2022年 / 12卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

Allylation; Boron; Catalysis; Transborylation; Ketone; ASYMMETRIC ALLYLBORATION; CARBONYL-COMPOUNDS; ALDEHYDES; HYDROBORATION; ORGANOBORANES; DERIVATIVES; ACTIVATION; REDUCTION; MECHANISM; ALCOHOLS;

D O I：

10.1021/acscatal.2c03158

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The diastereo-and enantioselective allylation of ketones remains a synthetic challenge, with transition metal catalysis offering the most applied methods. Here, a boron-catalyzed allylation of ketones with allenes is presented. Excellent yield, regioselectivity, and diastereoselectivity were found across function-alized substrates. The reaction was further developed to accommodate an enantioenriched boron catalyst and thus gave asymmetric ketone allylation in good yield, diastereoselectivity, and enantioselectivity. Mechanistic studies supported a hydroboration- allylation-transborylation pathway.

引用

页码：10887 / 10893

页数：7

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