Enantioselective C-C bond formation as a result of the oriented prochirality of an achiral aldehyde at the single-crystal face upon treatment with a dialkyl zinc vapor.

Tsuneomi Kawasaki,Sayaka Kamimura,Kenso Soai,Ai Amihara,Kenta Suzuki

doi:10.1002/anie.201102031

Tsuneomi Kawasaki, Sayaka Kamimura + Show 3 more

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https://doi.org/10.1002/anie.201102031

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Abstract

Enantioselective C-C bond formation as a result of the oriented prochirality of an achiral aldehyde at the single-crystal face upon treatment with a dialkyl zinc vapor.

Highlights

Lahav,[4e] Holland and Richardson[11] originally suggested the concept of a reaction at the enantiotopic face of an achiral single crystal[11a] and later reported oxidation reactions of olefinic compounds.[11b]
We report the enantioselective addition of diisopropylzinc at a particular single-crystal face of aldehyde 1 to form a chiral secondary alcohol 2 (Scheme 1)
We previously reported that 2-(alkylethynyl)- and 2(trialkylsilylethynyl)pyrimidine-5-carbaldehyde[15] serve as excellent substrates in asymmetric autocatalysis with the amplification of enantiomeric excess.[16]

Summary

Introduction

Lahav,[4e] Holland and Richardson[11] originally suggested the concept of a reaction at the enantiotopic face of an achiral single crystal[11a] and later reported oxidation reactions of olefinic compounds.[11b]. We report the enantioselective addition of diisopropylzinc (iPr2Zn) at a particular single-crystal face of aldehyde 1 to form a chiral secondary alcohol 2 (Scheme 1). When a single-crystal surface was treated with iPr2Zn vapor, the enantioselective isopro-

Results

Conclusion