Stereoselective bidirectional synthesis of spiroacetals via Rh(II)-catalysed double C–H insertion |
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Authors: | Romain J Lepage Mark J Coster |
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Institution: | Griffith Institute for Drug Discovery (GRIDD), Griffith University, Don Young Rd, Nathan, Queensland 4111, Australia |
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Abstract: | The stereoselective synthesis of 5,5-spiroacetals by Rh(II)-catalysed double C–H insertion of methylene acetals bearing two diazo ester substituents is described. The diastereoselectivity of this bidirectional approach can be tuned through appropriate choice of catalyst, and chiral catalysts lead to products with up to 89% ee. The diastereoselectivity of the first cyclisation suggests that the second cyclisation proceeds via a non-concerted pathway. |
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Keywords: | Spiroacetal Bidirectional C–H insertion Stereoselectivity Rh(II)-catalysis |
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