Journal
ORGANIC LETTERS
Volume 24, Issue 23, Pages 4246-4251Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01559
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Funding
- NSFC [22071210, 91956114]
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
- Natural Science Foundation of Jiangsu Province [BK20210849]
- Postgraduate Research & Practice Innovation Program of Jiangsu Province [KYCX21_2782]
- Shenzhen Science and Technology Innovation Committee [JCYJ20200109141408054]
- Innovation and Technology Commission (ITC) [CNERC14SC01]
- Hong Kong Research Grants Council [16303420, 16309321]
- Innovation & Entrepreneurship Talents Plan of Jiangsu Province [JSSCRC2021536]
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A catalytic asymmetric allylic substitution/isomerization process with central chirality transposition has been developed. This process utilizes the ambident reactivity of the 2-indole imine methide generated in situ from racemic tertiary indolylmethanols, allowing regioselective formation of a C-C bond at the 3 position and enantiocontrolled construction of a stereogenic center at the 2-benzylic position.
We have developed a catalytic asymmetric allylic substitution/isomerization process with central chirality transposition. This process takes advantage of the ambident reactivity of the 2-indole imine methide generated in situ from racemic tertiary indolylmethanols. The use of a suitable chiral phosphoric acid catalyst and an ortho-directing group allowed regioselective formation a C-C bond at the 3 position but enantiocontrolled construction of a stereogenic center at the 2-benzylic position.
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