Journal
CHEMICAL SCIENCE
Volume 9, Issue 22, Pages 4992-4998Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc00827b
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Funding
- State Key Laboratory of Organometallic Chemistry
- Hundred Talents Plan of Chinese Academy of Sciences
- Thousand Youth Talents Plan
- Shanghai Sailing Program [17YF1424100]
- National Natural Science Foundation of China [21702222]
- Science and Technology Commission of Shanghai Municipality [17JC1401200]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- Shanghai Institute of Organic Chemistry
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Catalytic chemo-and enantioselective generation of tertiary benzylic copper complexes from Cu-B(pin) (pin = pinacolato) additions to 1,1-disubstituted alkenes followed by in situ reactions with ketones and carboxylic acid phenol esters to construct multifunctional alkylboron compounds that contain quaternary stereogenic centers is presented. The method is distinguished by the unprecedented reaction mode of tertiary benzylic Cu complexes, allowing reaction with a wide range of carbonyl electrophiles in good yields and with high chemo-, site-, diastereo- and enantioselectivity. The catalytic protocol was performed with easily accessible chiral ligands and copper salts at ambient temperature. Functionalization of multifunctional alkylboron products provides useful building blocks that are otherwise difficult to access.
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