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

Abstract:

: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.

journal_name

Chirality

journal_title

Chirality

authors

Gawroński J,Gawrońska K,Kwit M,Kacprzak K,Rychlewska U

doi

10.1002/chir.20059

subject

Has Abstract

pub_date

2004-08-01 00:00:00

pages

405-13

issue

7

eissn

0899-0042

issn

1520-636X

journal_volume

16

pub_type

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