立体选择性
化学
催化作用
酒
药物化学
组合化学
立体化学
有机化学
作者
Chaofan Xu,Joseph Tassone,Brandon Q. Mercado,Jonathan A. Ellman
标识
DOI:10.1002/anie.202202364
摘要
Abstract An efficient and stereoselective Co III ‐catalyzed sequential C−H bond addition to 1,3‐enynes and aldehydes is disclosed. This transformation represents the first example of sequential C−H bond additions to 1,3‐enynes and a second coupling partner and provides the first example of preparing allenes by C−H bond addition to 1,3‐enynes. A wide range of aldehydes, C−H bond substrates and 1,3‐enynes with large substituents on the alkynes are effective substrates. The allenyl alcohol products can be further converted to dihydrofurans with high stereoselectivity either in situ or under Ag‐mediated cyclization conditions. The allenyl silyl group can also be transferred to the adjacent alcohol by a Brook rearrangement. Moreover, a mechanism for the transformation is proposed supported by X‐ray structural characterization of a cobaltacycle intermediate.
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