Double asymmetric induction during addition of chiral phosphites to C=N bond

Full text of DOI:10.1080/10426500213419

Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: http://www.tandfonline.com/loi/gpss20
Double Asymmetric Induction During Addition of
Chiral Phosphites to C=N Bond
Sheiko Sergei , Guliaiko Irina , Grushkun Evgeni & Oleg I. Kolodiazhnyi
To cite this article: Sheiko Sergei , Guliaiko Irina , Grushkun Evgeni & Oleg I. Kolodiazhnyi
(
2002) Double Asymmetric Induction During Addition of Chiral Phosphites to C=N Bond,
Phosphorus, Sulfur, and Silicon and the Related Elements, 177:8-9, 2269-2270, DOI:
0.1080/10426500213419
1
To link to this article: http://dx.doi.org/10.1080/10426500213419
Published online: 27 Oct 2010.
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Date: 13 June 2016, At: 06:51

Phosphorus, Sulfur and Silicon, 2002, Vol. 177:2269–2270
Copyright �C 2002 Taylor & Francis
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042-6507/02 $12.00 + .00
DOI: 10.1080/10426500290105997
DOUBLE ASYMMETRIC INDUCTION DURING
ADDITION OF CHIRAL PHOSPHITES TO
C N BOND
Sheiko Sergei, Guliaiko Irina, Grushkun Evgeni,
and Oleg I. Kolodiazhnyi
Institute of Bioorganic Chemistry, National Academy of Sciences
of Ukraine, Kiev, Murmanskaia,1
(Received July 29, 2001; accepted December 25, 2001)
We found that the addition of chiral di- or trialkylphosphites 1,2
�
1
[
R O (1R,2S,5R)-menthyl, (1S)-endo-bornyl,glucofuranosyl, etc) to
chiral C N compounds is accompanied by double asymmetric induction
�
at the �-carbon atom ( ) to give aminophosphonic acids with � 100% de
in case of matched pairs and 80–90% de in case of mismatched pairs as
1
,2
shown in the scheme. We found also that di- and trialkylphosphites
1
,2 furnish the aminosphosphonic acids with antipodal configuration.3
Configurations of new stereogenic centers were determined by chem-
ical methods, NMR and, in some cases X-ray analysis. N-substituted
aminophosphonic acids have been debenzylated by catalytic hydrogena-
tion with Pd-C and converted to 1-aminobenzylphosphonic acids of well-
known configuration.
Address correspondence to Prof. O. I. Kolodiazhnyi. E-mail: oikol123@bpci.kiev.ua
2
269

2
270
S. Sergei et al.
REFERENCES
[
1] O. I. Kolodiazhnyi, S. Yu. Sheiko, and E. V. Grishkun, Heteroatom Chemistry, 11,
38–143 (2000).
1
[
[
2] O. I. Kolodiazhnyi and S. Yu. Sheiko, Zh.obshch.khim., 71, 1039 (2001).
3] S. Yu. Sheiko, Ph.D. Thesis, Kiev, 1–130 (2002).