N‑Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N‑Boc Ethyl Oxamate
We report the practical, scalable synthesis of a range of N-methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N-Boc ethyl oxamate to deliver the corresponding N-Boc allylic amines, including in enantiopure form via ste...
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| Published in: | Journal of organic chemistry Vol. 86; no. 12; pp. 8538 - 8543 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
American Chemical Society
18-06-2021
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| Online Access: | Get full text |
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| Summary: | We report the practical, scalable synthesis of a range of N-methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N-Boc ethyl oxamate to deliver the corresponding N-Boc allylic amines, including in enantiopure form via stereospecific substitution. Subsequent N-methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts. This method solves the problem of converting commercially available alcohols into often volatile N-methyl allylic amines, many of which have limited commercial availability. |
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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/acs.joc.1c00918 |