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Structure and unexpected chiroptical properties of chiral 4‐pyrrolidinyl substituted 2(5 H )‐furanones
Author(s) -
Gawroński Jacek,
Gawrońska Krystyna,
Kwit Marcin,
Kacprzak Karol,
Rychlewska Urszula
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20059
Subject(s) - chemistry , chirality (physics) , stereochemistry , circular dichroism , combinatorial chemistry , computational chemistry , chiral symmetry , quantum mechanics , physics , nambu–jona lasinio model , quark
Planar 2(5 H )‐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 sp 2 character from the plane defined by the 2(5 H )‐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(5 H )‐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–π* and π–π* transition Cotton effects is determined primarily by the previously postulated allylic helicity rule. Chirality 16:405–413, 2004. © 2004 Wiley‐Liss, Inc.