Journal
ORGANIC LETTERS
Volume 15, Issue 9, Pages 2254-2257Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400822m
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Funding
- National Natural Science Foundation of China [21232006]
- National Basic Research Program of China [2011CB808700]
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An efficient bimetallic Zn(II)/Cu(I)-mediated asymmetric synthesis of simple axially chiral allenes from terminal alkynes and aldehydes was realized by taking advantage of the chiral amine (S)-alpha,alpha-diphenylprolinol 3. This one-pot procedure is compatible with broad scopes of both terminal alkynes and aldehydes, providing axially chiral allenes in practical yields with an excellent enantioselectivity. Control experiments revealed that CuBr is responsible for the efficient formation of propargylic amine while the combination of CuBr and ZnBr2 plays crucial roles in the amine-to-allene transformation.
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