Epoxidation of 8a-Alkyl-1,2,3,4,6,8a-hexahydronaphthalen-1-ones and -1-ols

Abstract

The regio- and diastereoselectivities of the epoxidations of decalin-1,4-dienones and dienols obtained from the Birch reductive alkylation of different α-tetralones is described. They appear to depend on the steric approach control of the peroxide and show an important contribution to the directing effect of homoallylic alcohols.

Key words

Birch alkylation - decalins - 1,4-dienes - epoxidation - directing effect

References

• 1a Vila AJ. Cravero RM. González-Sierra M. Tetrahedron Lett.  1991,  32:  1929 
• 1b Vila AJ. Cravero RM. González-Sierra M. Tetrahedron  1993,  49:  4511 
• 1c Labadie GR. Cravero RM. González-Sierra M. Synth. Commun.  1996,  26:  4671 
• 1d Lo Cascio A. Labadie GR. González-Sierra M. Cravero RM. Org. Prep. Proc. Intl.  2000,  32:  298 
• 2a Berti G. Top. Stereochem.  1973,  7:  93 
• 2b Rao AS. Paknikar SK. Kirtane JG. Tetrahedron  1983,  39:  2323 
• 3 Schultz AG. Harrington RE. Tham FS. Tetrahedron Lett.  1992,  33:  6097 
• 4 La Clair JJ. Lansbury PT. Zhi B-X. Hoogsteen KJ. J. Org. Chem.  1995,  60:  4822 
• 5 Van Hifte L. Little RD. Peterson JL. Moeller KD. J. Org. Chem.  1987,  52:  4647 
• 6 Brougham P. Cooper MS. Cummerson DA. Heaney H. Thompson N. Synthesis  1987,  1015 
• 7 Anderson WK. Veysoglu T. J. Org. Chem.  1973,  38:  2267 
• 8 Ituma M. Ziffer H. J. Org. Chem.  1979,  44:  1351 
• 9 Labadie GR. Cravero RM. González-Sierra M. Synth. Commun.  2000,  30:  4065 
• 10 Paquette LA. Barett JH. Org. Synth.  1969,  49:  62 
• 11a Heatcock CH. Amano Y. Tetrahedron  1968,  24:  4917 
• 11b Holbert GW. Ganem B. Engen DV. Clardy J. Borsub L. Chantrapromma K. Sadavongvivad C. Thebtaranonth Y. Tetrahedron Lett.  1979,  43:  715 
• 14 Hoveyda AH. Evans DA. Fu GC. Chem. Rev.  1993,  93:  1307 
• 15a Cragg GM. Meakins GD. J. Chem. Soc.  1965,  2554 
• 15b Bingham KD. Meakins GD. Wicha JJ. J. Chem. Soc.  1969,  510 
• 16a Baker AJ. Goudie AC. J. Chem. Soc., Chem. Commun.  1972,  951 
• 16b Zhurkovich IK. Ioffe DV. J. Org. Chem. USSR (Engl. Transl.)  1974,  10:  216 
• 16c Beckwith ALJ. O"Shea DM. Roberts DH. J. Am. Chem. Soc.  1986,  108:  6408 
• 17 Chu-Moyer MY. Danishefsky SJ. Schulte GK. J. Am. Chem. Soc.  1994,  116:  11213 

12

Unpublished results

13

Structures 2aα and 2aβ were optimized with AM1 as implemented in HyperChem^® 5.1, using an algorithm of conjugate gradient (Polak-Riviere)