Journal
ORGANIC LETTERS
Volume 21, Issue 18, Pages 7415-7419Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02726
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Funding
- National Natural Science Foundation of China [21502043, 21871128]
- Special Funds of the Taishan Scholar Program of Shandong Province [tsqn201812047]
- Natural Science Foundation of Shandong Province [ZR2017JL011]
- Shenzhen Innovation of Science and Technology Commission [JCYJ20170817110526264, ZDSYS201802081843490]
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A remote stereocontrolled 1,8-conjugate addition of thiazolones to propargylic aza-p-quinone methides formed from propargylic alcohols has been developed with the aid of a chiral phosphoric acid, and this represents the first report on organocatalytic stereocontrolled 1,8-addition of propargylic aza-p-quinone methides. Notably, the remote stereocontrolled activation protocol enables the construction of vicinal sulfur-containing quaternary carbon stereocenters and axially chiral tetrasubstituted allenes and promotes the chemistry of chiral phosphoric acids.
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