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Structure and unexpected chiroptical properties of chiral 4-pyrrolidinyl substituted 2(5H)-furanones

✍ Scribed by Jacek Gawroński; Krystyna Gawrońska; Marcin Kwit; Karol Kacprzak; Urszula Rychlewska

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
537 KB
Volume
16
Category
Article
ISSN
0899-0042

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✦ Synopsis

Planar 2(5H)-furanones substituted at C4 with a chiral pyrrolidinyl group show CD spectra which are apparently due to the distortion of the C4-N1 bond of sp2 character from the plane defined by the 2(5H)-furanone ring atoms and/or due to the presence of substituents in the pyrrolidine ring. This is a new, previously not encountered structural factor determining the chiroptical properties of 2(5H)-furanones and emerging from the analysis of X-ray diffraction data and quantum mechanical DFT computations. In the presence of a C5 pseudoaxial substituent in the furanone ring, the sign of the furanone n-pi* and pi-pi* transition Cotton effects is determined primarily by the previously postulated allylic helicity rule.

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