Enamines. VI The reaction of enamines with schiff bases and its stereochemistry.
β Scribed by Shuji Tomoda; Yoshito Takeuchi; Yujiro Nomura
- Publisher
- Elsevier Science
- Year
- 1969
- Tongue
- French
- Weight
- 199 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Although enamines are known to be excellent addends in many Michael type reactions, the reaction of enamines with Schiff bases has hitherto never been found in the literatures. We now would like to report the reaction and its stereochemical consequence.
Reaction of 1-morpholino-l-cyclohexene (Ia) or 1-morpholino-4-tert.-butyl-I-cyclohexene (Ib) with benzylideneaniline (II) was carried out at room temperature by standing overnight in absolute methanol. Substituted enamines (IIIa,b) were obtained (yield; about 30%) whose structures were confirmed by elementary
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Acetophenolle anilreactedwith cna mole ofPCCl53DM, inIMP2, and afforded after treawt rith perohlorio acid, the salt Ia, m.p. 160Β°, which upcm azlrrlina i&ydrol,ymir,gmva the x-for@m"ldnrr IIa3,B.p.1300. Tbs mtxuoture of IIaru inferred frcm ita IR (1660 or?) and lDllIL rpectra (CDC13)r ai@alm at 4.5
It fs shown that the reactfvfty towards electrophftes of dfastereomerfc Sckfff bases of \*R and \*S vatfne, leucfne, phenylalanfne and norvalfne methyl esters wfth (lS,ZS,SS) or (lR,2R,SR) 2-hydroxy 3-pfnanone, is hfghly dependent on the stereochemistry of the startfng product.