Journal
ORGANIC LETTERS
Volume 18, Issue 6, Pages 1230-1233Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03681
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Funding
- Indo-US Science and Technology Forum, India
- NIHGM1106S1 [GM1106S1]
- ACS-PRF [51785]
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Chiral ammonium salts were used to catalyze the isomerization of organomanganese-complexed alkynyl aldehydes to chiral allenal building blocks in moderate to good enantiomeric excesses. Normally, conjugated alkynyl aldehydes do not isomerize to their thermodynamically less stable allene isomers. However, with a manganese auxiliary in place to promote allene formation, asymmetric protonation of cumulenolate intermediates was realized using a variety of cinchonidinium salts in a weakly basic biphasic reaction system. Optimal results were realized using a novel cinchonidinium geranyl derivative with its C-9 hydroxyl group playing a crucial role in enantioselectivity.
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