ISSN:
0009-2940
Keywords:
Homoenolate equivalents, chiral
;
Hydroxyalkylation
;
1-Aminoallyl anions, chiral
;
Acetoxy ketones, chiral
;
Homoaldol reaction, chiral
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The hydroxyalkylation of lithiated 3-[(S)-2-(methoxymethyl)-pyrrolidino]-1,3-diphenylpropene (2) with aldehydes is completely regioselective giving homoaldol adducts in good yields. The simple diastereoselectivity is low with typical ratios ranging between 1:1 and 1:3 with the syn isomer predominating. The induced diastereoselectivity is much higher and is strongly solvent-dependent. The reaction predominantly proceeds according to a metalloretentive mechanism from the si side of the allylic system in THF as well as in TBME. The induced diastereoselectivity obtained by the use of the less solvating TBME is considerably higher than in the strongly solvating THF, selectivities of up to 97% ee being reached.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19961291004
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