A convenient preparation of β-amino alcohols from epoxides and halomagnesium alkylamides
✍ Scribed by M.C. Carre; J.P. Houmounou; P. Caubere
- Book ID
- 104228782
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 188 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
T~~ecLtmeti 06 epotiden with hdeomagnenium a.Lk+!tamiden in TffF addoh& the coh.ttiponding @amino a&oh& in good GM&. The B-amino alcohol sequence plays a very important part in organic as well as in Medicinal Chemistry.I The simplest classical method for preparing B-amino alcohols consists in heating an epoxide with an amine. 2 This preparation is somewhat limited with poorly nucleophilic amines. 2,3 Moreover, drastic conditions being often involved, ~$4 further limitations are encountered with sensitive epoxides. Current studies in our laboratory require the preparation of polycyclic B-amino alcohols of which some examples will be given further on. In numerous cases, we found the classical epoxide aminolysis completely Useless. Among the other methods developed in order to promote the reaction of amines with epoxides5 we were particularly attracted by the results obtained by Overman and Flippin who efficiently used diethylaluminium amides.6 The only drawback, esuecially when large scale preparations are needed, lies in using Et3A1. It might be thought that aminomagnesium derivatives, easily prepared from the corresponding amine and ethyl magnesium bromide, could be advantaqeously used in place of aluminium amides. Indeed amino-magnesium derivatives are generally considered as strong bases. However it might be expected that the somewhat covalent character of the nitrogen-magnesium bond could be sufficient to confer to magnesium amides efficient nucleophilic reactivity towards enoxides. This hypothesis was completely verified and we report in the present letter that halomagnesium alkylamides react with epoxides under mild conditions to give, after hydrolysis B-amino alcohols in good yields.
📜 SIMILAR VOLUMES
Cu( OTf)z=catalyzed ring-opening of epoxides with anilines: A convenient synthesis of p-amino alcohols HOU, Xue-Long\*(#ZltR) W, Jie(!&M) DAI, Li-Xin(#P@) f . a ~t w v of +~omctdlic Chemi~trv, Shanghai InatitUteof Chyanu Chcmutry, C h i n u c Academy of Seimar, Shanghai 600082, Chino Aktrmzt by copp
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