Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 49, Pages 15422-15425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b11418
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Funding
- Japan Society for the Promotion of Science (JSPS), Global COE Program
- University of Tokyo, MEXT, Japan
- Japan Science and Technology Agency (JST)
- JSPS
- Grants-in-Aid for Scientific Research [15H06134, 15H05698, 15J11753] Funding Source: KAKEN
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Acicular purplish crystals were obtained from Cu(acac)(2) and a chiral bipyridine ligand. Although the crystals were not soluble, they nevertheless catalyzed asymmetric silyl conjugate addition of lip ophilic substrates in water. Indeed, the reactions proceeded efficiently only in water; they did not proceed well either in organic solvents or in mixed water/organic solvents in which the catalyst/substrates were soluble. This is in pronounced contrast to conventional organic reactions wherein the catalyst/substrates tend to be in solution. Several advantages of the chiral Cu(II) catalysis in water over previously reported catalyst systems have been demonstrated. Water is expected to play a prominent role in constructing and stabilizing sterically confined transition states and accelerating subsequent protonation to achieve high yields and enantioselectivities.
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