期刊
ORGANIC LETTERS
卷 19, 期 16, 页码 4355-4358出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02063
关键词
-
资金
- NIH [R01 GM111820, NSF CHE0421224, CHE1229234, CHE0840401, CHE1048367, NIH P20 GM104316, P20 GM103541, S10 OD016267]
- UD
- UD Plastino Alumni Undergraduate Research Fellowship programs
- NSF
Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.
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