Journal
ORGANIC LETTERS
Volume 24, Issue 16, Pages 3080-3085Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01082
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Funding
- Ministry of Education of Singapore [A-0004102-00-00]
- Singapore National Research Foundation, Prime Minister's Office for the NRF Investigatorship Award [A-0004067-00-02]
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Asymmetric palladium-catalyzed arylboration/cyclization of both nonactivated and activated alkenes with B2pin2 was developed to synthesize borylated 3,4-dihydroisoquinolinones and oxindoles with high yields and high enantioselectivities. The synthetic utility of this enantioselective protocol was demonstrated by synthesizing various chiral derivatives containing quaternary stereogenic carbon centers, including the enantioenriched Roche anticancer agent (S)-RO4999200.
Asymmetric palladium-catalyzed arylboration/cyclization of both nonactivated and activated alkenes with B2pin2 was developed. A wide range of N-allyl-o-iodobenzamides and o-iodoacryanilides reacted with B2pin2 to afford borylated 3,4-dihydroisoquinolinones and oxindoles, respectively, in high yields with high enantioselectivities. The synthetic utility of this enantioselective protocol was highlighted by synthesizing various chiral 3,4-dihydroisoquinolinone and oxindole derivatives containing quaternary stereogenic carbon centers, including enantioenriched Roche anticancer agent (S)-RO4999200.
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