ISSN:
1434-193X
Keywords:
Iminium ion
;
Propargylsilane
;
Pipecolic acid derivative
;
Amino acids
;
Asymmetric synthesis
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Addition of a propargylsilane moiety onto chiral cyclic iminium ions occurs with a high level of stereoselectivity intermolecularly as well as intramolecularly. This operation generates allenic α-amino acids precursors. An isomerization leading to a 1,3-dienyl compound precludes the formation of an allenic amino acid in the acyclic series; however, this isomerization did not take place with the cyclic α-amino ester which was thus obtained with a 55 % ee. AM1 calculations explain the difference of reactivity between cyclic and acyclic compounds on a conformational basis.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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