3
124
J. M. Hopkins et al.
LETTER
the latter ligands were used. The most significant result
was with the case of the intramolecular double Heck/Mi-
zoroki cyclization (Table 3) in which (S)-3,3¢-di-Oi-Pr-
BINAP (5) gave product (R)-17 with approximately the
same ee (%) as that of (S)-BINAP (Table 3) but with the
opposite configuration. Further applications of ligands 4–
(5) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989,
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(6) Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org.
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7
and the preparation of 3,3¢-disubstituted BINAP deriva-
tives not containing an oxygen atom directly bonded to
the naphthalene rings are currently underway.
(8) (a) Andersen, N. G.; Parvez, M.; McDonald, R.; Keay, B. A.
Can. J. Chem. 2004, 82, 145. (b) Andersen, N. G.;
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Acknowledgment
Lett. 2000, 2, 2817. (d) Che, D.; Andersen, N. G.; Lau, S. Y.
W.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 2000,
Merck Frosst Canada and the Natural Sciences and Engineering
Research Council of Canada (NSERC) through a CRD grant are
thanked for financial support. In addition, NSERC and the Alberta
Ingenuity Fund are thanked for postgraduate scholarships to J.M.H.
and B.M.M.W.
11, 1919.
(
9) (a) Gorobets, E.; Parvez, M.; Wheatley, B. M. M.; Keay, B.
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3
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Synlett 2006, No. 18, 3120–3124 © Thieme Stuttgart · New York