ISSN:
0009-2940
Keywords:
Addition Stereoselective, nonchelation-controlled
;
Reagent, organozinc
;
Stereodifferentiation, double
;
Oligo(tetrahydrofuran)
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The additions of the enantiomerically pure organozinc reagents 17 and 33 to the THF-aldehyde 1 in the presence of the monodentate Lewis acid boron trifluoride - ether give the nonchelation-controlled addition products 7 and 36, respectively (stereoselectivity 95:5, 86:14). These results provide a route to oligo(tetrahydrofuran)s with the relative stereochemistry trans-syn-cis. A stereodirecting effect of the chiral center in the organozinc reagent 17 is found, leading to simple diastereoselectivies in the reaction with achiral aldehydes and to a matched-mismatched case in the reaction with the chiral aldehyde 1.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270819
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