Unprecedented Stereochemical Reversal from Alkyl to Aryl Substituents in the Johnson-Claisen Rearrangement of Methyl 3-Hydroxy-2-methylenealkanoates

Synlett

Volumn 1996, Issue 8, 1996, Pages 747-748

  Basavaiah, D ^a   Pandiaraju, S ^a   Krishnamacharyulu, M ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002871273     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5524     Document Type: Article

References (19)

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9. We have very recently described a simple and convenient synthesis of functionalized trisubstituted alkenes, i.e. (4Z)-4-cyanoalk-4-enoates via the Johnson-Claisen rearrangement of the Baylis-Hillman adducts (3-hydroxy-2-methylenealkanenitriles). see Basavaiah, D.; Pandiaraju, S. Tetrahedron Lett., 1995, 36, 757.
10. Drewes and coworkers reported that the Claisen orthoester rearrangement of alkyl 3-hydroxy-2-methylenepropionates with triethyl orthopropionate produced E/Z mixture of 2-methylpent-4-enoates. However this report did not provide any information either on E/Z ratio of resulting 2-methylpent-4-enoates or on substituent effect on stereochemistry see Drewes, S.E ; Emslie, N.D.; Karodia, N.; Loizou, G. Syn. Commun., 1990, 20, 1437.
11. Basavaiah, D.; Gowriswari, V.V.L. Tetrahedron Lett., 1986, 27, 2031.
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13. Basavaiah, D.; Sarma, P.K.S.; Bhavani, A.K.D. J. Chem. Soc. Chem. Commun., 1994, 1091.
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16. Fort, Y.; Berthe, M.C.; Caubere, P. Tetrahedron., 1992, 48, 6371.
17. 4 : C, 63.13; H, 8.83; found C, 63.16; H, 8.85.
18. 4: C, 68.68; H, 6.91; found C, 68.69; H, 6.89.
19. Referees have suggested this possibility.