Chiral phosphine ligand via cyclization of bis-alkenylphosphonate

Full text of DOI:10.1080/10426500213306

Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: http://www.tandfonline.com/loi/gpss20
Chiral Phosphine Ligand via Cyclization of Bis-
Alkenylphosphonate
Yasuo Nagaoka , Hideki Inoue & Kiyoshi Tomioka
To cite this article: Yasuo Nagaoka , Hideki Inoue & Kiyoshi Tomioka (2002) Chiral Phosphine
Ligand via Cyclization of Bis-Alkenylphosphonate, Phosphorus, Sulfur, and Silicon and the
Related Elements, 177:8-9, 1959-1960, DOI: 10.1080/10426500213306
To link to this article: http://dx.doi.org/10.1080/10426500213306
Published online: 27 Oct 2010.
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Date: 09 June 2016, At: 07:48

Phosphorus, Sulfur and Silicon, 2002, Vol. 177:1959–1960
C
Copyright 2002 Taylor & Francis
1042-6507/02 $12.00 + .00
DOI: 10.1080/10426500290094666
CHIRAL PHOSPHINE LIGAND VIA CYCLIZATION
OF BIS-ALKENYLPHOSPHONATE
Yasuo Nagaoka, Hideki Inoue, and Kiyoshi Tomioka
Kyoto University, Japan
(Received July 29, 2001; accepted December 25, 2001)
As our continuing studies of efficient synthetic application of lithium
phosphonates,1 we have developed cyclization reaction of bis-
alkenylphosphonate 1.2 Although the reaction of 1 with organolithium
reagents afforded both tandem Michael cyclization products and
-deprotonation-cyclization products,2 the latter was selectively formed
in high yield by simply treating 1 with LDA. Application of chiral bis-
alkenylphosphonate 2 opens a simple synthetic way to chiral phosphine
ligand 5.3, Treatment of 2 with LDA followed by electrophilic trapping
of intermediate cyclic lithium phosphonate 3 with benzaldehyde af-
forded aldol-type adduct 4 in 54%. The alcohol 4 was transformed to 5
by 6 steps in 16% yield.
SCHEME 1
A chiral phosphone 5 without two methoxy groups was developed by Minami as an
efficient ligand for the enantioselective allylic alkylation.
Address correspondence to Yasuo Nagaoka, Faculty of Engineering, Kansai Univer-
sity, Suita, Osaka 564-8680, Japan.
1959

1960
Y. Nagaoka et al.
REFERENCES
[1] Y. Nagaoka and K. Tomioka, J. Org. Chem., 63, 6428 (1998).
[2] Y. Nagaoka and K. Tomioka, Org. Lett., 1, 1467 (1999).
[3] T. Minami, Y. Umezu, S. Nishikawa, R. Mori, and Y. Nakayama, Tetrahedron
Asymmetry, 2, 667 (1991).