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Synfacts 2011(1): 0099-0099
DOI: 10.1055/s-0030-1259182
DOI: 10.1055/s-0030-1259182
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Organocatalytic Construction of Polycyclic Compounds
C. A. Leverett, V. C. Purohit, D. Romo*
Texas A&M University, College Station, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Dezember 2010 (online)
Significance
The catalytic asymmetric aldol lactonization of keto acids accessing bi- and tricyclic β-lactones is reported. The catalytic species, homobenzotetramisole (HMBT) 1, in combination with Hünig’s base, tosyl chloride as coupling reagent, and LiCl as a Lewis acid additive, provided the corresponding products in high yields and enantiopurities. Interestingly, the addition of LiCl proved to be crucial to obtain high yields, whereas the enantioselectivities showed somewhat decreased values under these conditions. This observation is rationalized by possible Li chelations or completely racemic pathways via acid chloride intermediates.