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参考文献
1) M. A. Brook, Silicon in Organic, Organometallic, and
Polymer Chemistry; John Wiley and Sons: New York
2000.
2) K. Igawa, K. Tomooka, Chiral Silicon Molecules in
Organosilicon Chemistry: Novel Approaches and
Reactions (Eds: Hiyama, T., Oestreich, M.), Chap. 14,
Wiley, Weinheim, Germany, 2019.
3) (a) K. Tomooka, A. Nakazaki, T. Nakai, J. Am. Chem.
Soc. 2000, 122, 408. (b) K. Igawa, J. Takada, T.
Shimono, K. Tomooka, J. Am. Chem. Soc. 2008, 130,
16132. (c) K. Igawa, D. Yoshihiro, N. Ichikawa, N.
Kokan, K. Tomooka, Angew. Chem. Int. Ed. 2012, 51,
12745.
4) (a) A. Nakazaki, T. Nakai, K. Tomooka, Angew. Chem.
Int. Ed. 2006, 45, 2235. (b) A. Nakazaki, J. Usuki, K.
Tomooka, Synlett 2008, 2064. (c) K. Igawa, N. Kokan,
K. Tomooka, Angew. Chem. Int. Ed. 2010, 49, 728.
5) K. Igawa, D. Yoshihiro, Y. Abe, K. Tomooka, Angew.
Chem. Int. Ed. 2016, 55, 5814.
令和 2 年度
九州大学大学院総合理工学報告 第 42 巻 第 2 号
6) K. Igawa, A. Kuroo, D. Yoshihiro, Y. Yamanaka, K.
Tomooka, Synlett 2017, 28, 2445.
7) O. Mitsunobu, Synthesis 1981, 1.
8) Selected Crystal Data for (SSi*,4R*)-4a: Triclinic, P ｰ 1
(No. 2), a = 6.619(3) Å, b = 7.239(4) Å, c = 21.720(12) Å, α = 86.28(5)°, β = 84.55(4)°, γ = 73.97(3)°, V = 994.9(9)
Å3, Z = 2, R1 = 0.1460, wR2 = 0.2104, CCDC 154693.
9) Study on stereoselectivity of Tsuji-Trost reaction, see:
(a) T. Hayashi, T. Hagihara, M. Konishi, M. Kumada,
J. Am. Chem. Soc. 1983, 105, 7767. (b) S.-I.
Murahashi, Y. Taniguchi, Y. Imada, Y. Tanigawa, J.
Org. Chem. 1989, 54, 3292. (c) K. L. Granberg, J.-E.
Bäckvall, J. Am. Chem. Soc. 1992, 114, 6858.
10) Compound data of (SSi,4R)-12a: 1H NMR (300 MHz,
CDCl3): δ 7.52-7.48 (m, 2H), 7.36-7.31 (m, 3H), 6.83
(dd, J = 9.9, 2.4 Hz, 1H), 6.22 (dd, J = 10.5, 2.4 Hz, 1H),
3.89 (m, 1H), 1.79(brs, 1H), 1.63 (dd, J = 14.7, 7.5 Hz,
1H), 0.96 (s, 9H), 0.66 (dd, J = 15.3, 5.7 Hz, 1H). 13C
NMR (75 MHz, CDCl3): δ 159.2, 136.0, 134.8, 129.0,
127.6, 126.7, 56.5, 27.0, 18.0, 16.9. IR (neat, cm–1):
2926, 2854, 1563, 1469, 1361, 1110, 822, 733, 700, 614.
HRMS (EI, positive): Exact mass calc. for C14H21NSi
[M]+, requires m/z: 231.1443, found m/z: 231.1442.
[α]D23 –89.9 (c 0.54, CHCl3) for >98% ee.
21
11) Compound data of (SSi,4R)-13a: 1H NMR (300 MHz,
CDCl3): δ 7.52 (m, 2H), 7.36-7.32 (m, 3H), 6.81 (dd, J =
10.2, 2.1 Hz, 1H), 6.24 (dd J = 10.2, 2,4 Hz, 1H),
3.15-3.10 (m, 1H), 2.60 (dd, J = 14.7, 6.3 Hz, 1H), 2.37
(dd, J = 14.7, 9.0 Hz, 1H), 1.39 (dd, J = 15.3, 8.4 Hz,
1H), 0.95 (s, 9H), 0.62 (dd, J = 15.3, 8.4 Hz, 1H). 13C
NMR (75 MHz, CDCl3): δ 178.2, 157.2, 136.3, 134.8,
129.0, 127.7, 127.3, 42.1, 41.0, 27.1, 17.0, 11.9. IR
(neat, cm–1): 2926, 2855, 1708, 1469, 1427, 1110, 822,
733, 699. HRMS (EI, positive): Exact mass calc. for
C12H13O2Si [M–tBu]+, requires m/z: 217.0685, found
m/z: 217.0685. [α]D26 –71.0 (c 0.66, CHCl3) for >98% ee.
12) Compound data of (SSi,4S)-13a: 1H NMR (300 MHz,
CDCl3): δ 7.53-7.50 (m, 2H), 7.37-7.32 (m, 3H), 6.84
(dd, J = 10.2, 2.1 Hz, 1H), 6.24 (dd, J = 10.2, 2.4 Hz,
1H), 3.20 (m, 1H), 2.50 (dd, J = 15.0, 6.3 Hz, 1H), 2.24
(dd, J = 15.3, 8.7 Hz, 1H), 1.44 (dd, J = 15.3, 8.1 Hz,
1H), 0.94 (s, 9H), 0.62 (dd, J = 15.0, 5.4 Hz, 1H). 13C
NMR (75 MHz, CDCl3): δ 178.6, 157.1, 136.8, 134.6,
129.0, 127.7, 127.4, 42.3, 41.7, 26.7, 15.7, 12.8. IR
(neat, cm–1): 2926, 1707, 1427, 1285, 1111, 822, 728,
699, 522. HRMS (EI, positive): Exact mass calc. for
C12H13O2Si [M–tBu]+, requires m/z: 217.0685, found
m/z: 217.0685. [α]D26 –16.7 (c 1.33, CHCl3) for >98% ee.
...