deprotected using Fukuyama’s method11 followed by a reaction
with phenyl isocyanate to give a chiral cyclic urea (Scheme 3). The
starting adduct, which was recovered from the reaction shown in
Scheme 1, was used for this reaction.
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Scheme 3 Transformation of the adduct of 1a to (DHQD)2AQN.
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102, 4263 (DHQD)2PHAL is a good chiral source for asymmet-
ric silylcyanation of ketones. See: S.-K. Tian, R. Hong and L.
Deng, J. Am. Chem. Soc., 2003, 125, 9900. However, (DHQD)2AQN
was better than (DHQD)2PHAL for the present asymmetric
induction.
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79.
In summary, this paper describes the asymmetric ring opening
of aziridines based on chiral recognition and sequential ring
opening. Although good methods have been in use for the
asymmetric ring opening of meso-aziridines thus far, this is the
first example presenting high selectivity for the ring opening of
terminal aziridines, and this method contributes to the supply of
a new series of chiral b-amino acids.
Notes and references
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Chem., 1994, 106, 625; D. Tanner, Angew. Chem., Int. Ed. Engl., 1994,
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in Comprehensive Heterocyclic Chemistry II, Vol. 1A (Eds.: A. R.
Katritzky, C. W. Rees and E. F. Scriven), Pergamon, Oxford, 1996,
pp. 1-60; (d) A. Padwa, A. D. Woolhouse, InComprehensive Heterocyclic
Chemistry Vol. 7 (Ed.: W. Lwowski), Pergamon, Oxford, 1984.
10 See Supporting Information for details†.
11 W. Kurosawa, T. Kan and T. Fukuyama, Org. Synth., 2004, 10, 482.
The deprotected product was not isolated and the resulting mixture
was treated with the isocyanate.
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