期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 47, 页码 14154-14158出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507373
关键词
alkynes; asymmetric catalysis; enantioselectivity; oxocarbenium ion; oxygen heterocycles
资金
- National Science Foundation [CAREER CHE 1151364]
- UD Chemistry and Biochemistry Plastino Alumni Undergraduate Research Fellowship program
- NSF [NSF CHE 0421224, CHE 1229234, CHE 0840401]
- NIH [NIH P20 GM103541, S10 RR02682, 5P30 GM110758]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1151364] Funding Source: National Science Foundation
An enantioselective, copper(I)-catalyzed addition of terminal alkynes to isochroman ketals to set diaryl, tetrasubstituted stereocenters has been developed. The success of this reaction relies on identification of a Cu/PyBox catalyst capable of distinguishing the faces of the diaryl-substituted oxocarbenium ion. This challenging transformation enables efficient conversion of readily available, racemic ketals into high-value enantioenriched isochroman products with fully substituted stereogenic centers. High yields and enantiomeric excesses are observed for various isochroman ketals and an array of alkynes.
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