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Synthesis of Some Optically Active α-Pyridyl-carbinols and Determination of Absolute Configuration from the CD of Their in situ Complexes with [MO₂(OAc)₄ ]

Nikolina Berova ; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, BG-1113 Sofia, (BG)
Stefan Bojadziev ; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, BG-1113 Sofia, (BG)
Rosiza Rakovska ; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, BG-1113 Sofia, (BG)
Jadwiga Frelek ; Chair of Natural Products Chemistry, Warsaw University, ul. Pasteurti 1, PL-02 093 Warszawa, (PL)
Gunther Snatzke ; Lehrstuhl fur Strukturchemie, Ruhruniversitat, Postfach 1021 48, D-4630 Bochum (F. R. Germany)

Sažetak

Four new a-pyridyl-aryl-carbinols have been synthesized, and
twelve such racemates have been for the first time resolved by
standard procedures. From the positive CD-couplet of the complex
between (S)-l and 23 an antiperiplanar arrangement of the
H-C(OH, Ph)-C.(Py)-N-moiety could be derived as the preferred
conformation. From the CD-spectra above 300 nm of this and seven
other compounds of known absolute configuration in the presence
of 23 the following correlation with stereochemistry was derived,
which was then applied to determining the absolute configuration
of fourteen other a-pyridyl-aryl-carbinols: for (R)-configuration
negative CD-bands appear between 500 to 510 (sometimes detectable
only as shoulder) and at 408 to 470 nm, between 335 to 380
nm apositive Cotton effect is registered, and another one shows
up below 320 nm, which has mostly apositive sign for secondary,
but anegative one for tertiary carbinols of the mentioned absolute
sense of chirality.

Ključne riječi

Hrčak ID:

175507

URI

https://hrcak.srce.hr/175507

Datum izdavanja:

10.8.1989.

Posjeta: 778 *