ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Enantioselective Synthesis of Allyl-, Propargyl-, and 4-En-2-ynyl-amines via 1,2-Addition of Organocerium Reagents to Chiral Aldehyde Imines(E)- and (Z)-Allyl-, propargyl-, and 4-en-2-ynyl-amines 5 and 14, useful bifunctional building blocks and of pharmaceutical interest, are synthesized in high enantiomeric purity (e.e. ≥ 97%). Key step is the diastereoselective 1,2-addition (d.e. 86 to ≥ 98%) of organocerium reagents to chiral α,β-unsaturated aldehyde imines 3 or 8 to produce adduct amines 4 and 9 (Schemes 1 and 4, resp.). The propargylamine 9 is a substrate for Pd-catalyzed coupling with alkenyl halides to produce the enynylamine 11a and the thienyl-substituted alkynylamine 11b. The chiral auxiliary (S,S)-2 is removed from 4 and 11 in 3 steps affording the title compounds 5 and 14. Diastereoisomer enrichment of the hydrochloride of 6 by crystallization is possible.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19950780419
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