ISSN:
0947-3440
Keywords:
Bicyclopropylidene
;
Spiro compounds
;
Cycloadditions
;
Amino acids
;
Cuprates
;
Tetrahydropyridines
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reactions of ethyl 2-acetoxy-2-diphenylmethyleneaminoacetate (1) with organocopper reagents derived from bicyclopropylidene (2) and methylenecyclopropane (3) are accompanied by an unusual mode of opening of one three-membered ring to give 4-methylene-1,2,3,4-tetrahydropyridine derivatives 8a, 9 in good yields. The cuprate derived from methylenespiropentane (4) reacts with 1 to yield both the normal substitution product 14 (37%) as well as the rearrangement product 15 (34%), while the simple cyclopropylcuprate undergoes substitution to give the protected cyclopropylglycine 16 (75%) without rearrangement. The tetrahydropyridine 8a shows an interesting tautomerism in solution. The 4-cyclopropylidenetetrahydropyridine 15 undergoes an unusual dehydrodimerization to produce two separable rotamers, C2-19 and C1-19, via 18.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719971105
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