One‐Pot Synthesis of N‐Substituted β‐Amino Alcohols from Aldehydes and Isocyanides |
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| Authors: | Răzvan C. Cioc Daan J. H. van der Niet Elwin Janssen Dr. Eelco Ruijter Prof. Dr. Romano V. A. Orru |
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| Affiliation: | Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands) |
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| Abstract: | A practical two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon–carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α‐halo ketones, β‐halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible. |
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| Keywords: | aldehydes amino alcohols isocyanide Lewis bases salbutamol |
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