Remote stereocontrol using rotationally restricted amides: (1,5)-Asymmetric induction

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8587-8590

  Clayden, Jonathan ^a   Darbyshire, Megan ^a   Pink, Jennifer H ^a   Westlund, Neil ^a   Wilson, Francis X ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMIDE;

ARTICLE; CRYSTAL STRUCTURE; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030721030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10289-1     Document Type: Article

References (28)

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17. The enolates of ketones 1 were particularly unreactive: lithium and sodium enolates could not be alkylated, and the potassium enolate reacted only at temperatures over 0 °C
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21. The barriers to epimerisation were calculated by following the interconversion of the atropisomers in dioxane solution using HPLC. Full details will be published later.
22. 3SiCl is pure Z) would give syn-7, and molecular modelling (Macromodel-MM2) finds anti-7 to be the lower energy atropisomer.
23. -1 greater than those of the diethylnaphthamides, with the difference greatest with smaller 2-substituents; we expect this trend to continue with the "diisoheptyl" naphthamides, hence the increased stability of 7 over 3.
24. Clark, R. D.; Jahangir, A. Org. Reac. 1995, 47, 1.
25. Clark, R. D.; Jahangir. J. Org. Chem. 1989, 54, 1174.
26. The 2,4,6-trimethylbenzamide 14 was made by stirring mesitoyl chloride with excess diisopropylamine.
27. The 2,4,6-triethylbenzamide 17 was made from 1,3,5-triethylbenzene by either of the routes shown below (see Fuson, R. C.; Corse, J. J. Am. Chem. Soc., 1938, 60, 2063). (figure presented)
28. The symmetry of the compound tells us only the relative stereochemistry of the 1,5-related stereogenic centres. The stereochemistry of the stereogenic but achirotopic aryl-carbonyl bond is assigned on the basis of work described in reference 14.