The First Enantiomerically Pure Triangulane (M)-Trispiro.

作者信息

Khlebnikov AF, Kostikov RR, Kozhushkov SI, Schreiner PR, Wittkopp A, Yufit DS

机构信息

Institut für Organische Chemie der Universität, Tammannstrasse 2, D-37077 Göttingen (Germany).

出版信息

Angew Chem Int Ed Engl. 1999 Dec 3;38(23):3474-3477. doi: 10.1002/(sici)1521-3773(19991203)38:23<3474::aid-anie3474>3.3.co;2-y.

DOI:10.1002/(sici)1521-3773(19991203)38:23<3474::aid-anie3474>3.3.co;2-y

PMID:10602212

Abstract

A remarkably high specific rotation, even at 589 nm, is shown by (M)-1, the first enantiomerically pure unbranched [4]triangulane, although it has no chromophore that would lead to any significant absorption above 200 nm. This outstanding rotatory power is in line with a helical arrangement of its sigma bonds, as confirmed by high-level computations. Thus, it is appropriate to call (M)-1 a "sigma-[4]helicene", the first sigma-bond analogue of the aromatic [n]helicenes.

摘要