An asymmetric synthesis of (2S,5S)-5-substituted azepane-2-carboxylate derivatives |
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Authors: | Wishka Donn G Bédard Marion Brighty Katherine E Buzon Richard A Farley Kathleen A Fichtner Michael W Kauffman Goss S Kooistra Jaap Lewis Jason G O'Dowd Hardwin Samardjiev Ivan J Samas Brian Yalamanchi Geeta Noe Mark C |
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Institution: | Pfizer Worldwide Research and Development, Eastern Point Rd., Groton, Connecticut 06340, USA. donn.g.wishka@pfizer.com |
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Abstract: | To facilitate a drug discovery project, we needed to develop a robust asymmetric synthesis of (2S,5S)-5-substituted-azepane-2-carboxylate derivatives. Two key requirements for the synthesis were flexibility for elaboration at C5 and suitability for large scale preparation. To this end we have successfully developed a scalable asymmetric synthesis of these derivatives that starts with known hydroxy-ketone 8. The key step features an oxidative cleavage of aza-bicyclo3.2.2]nonene 14, which simultaneously generates the C2 and C5 substituents in a stereoselective manner. |
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