Organic Letters
Letter
For Z = SO2Ph, see: (e) Ding, Z.; Yang, J.; Wang, T.; Shen, Z.; Zhang, Y.
Chem. Commun. 2009, 5, 571−573. For Z = SO2NHPh, see: (f) Geng,
Z.; Wu, Y.; Miao, S.; Shen, Z.; Zhang, Y. Tetrahedron Lett. 2011, 52,
907−909. For Z = CH(OH)CF3, see: (g) Cotman, A. E.; Cahard, D.;
Mohar, B. Angew. Chem., Int. Ed. 2016, 55, 5294−5298. For Z = Hetaryl,
see: (h) Vyas, V. K.; Bhanage, B. M. Org. Lett. 2016, 18, 6436−6439.
(11) Rast, S.; Modec, B.; Stephan, M.; Mohar, B. Org. Biomol. Chem.
2016, 14, 2112−2120.
(12) (a) Turek, M.; Szczęsna, D.; Koprowski, M.; Bałczewski, P.
Beilstein J. Org. Chem. 2017, 13, 451−494. (b) Gabriele, B.; Mancuso, R.;
Veltri, L. Chem. - Eur. J. 2016, 22, 5056−5094.
(14) dr’s correspond to the respective ratios of cis,trans-, cis,cis-,
trans,trans-, and trans,cis-2a (trans,cis-2a not formed). For their
(15) Though identical diastereo- and enantioselectivities were
obtained using either cat. A or B, the reduction was somewhat faster
with B.
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(16) Similarly as for the substrate 1a, exposing 1e (dr = 97:3) to
1
DCO2D/Et3N 3:2 in CDCl3 at 60 °C revealed by H NMR a fast
deuterium exchange (within 10 min) at C2 and C3.
(17) Noteworthy, exposure of 1m to HCO2H/Et3N 3:2 at 60 °C
(without catalyst) resulted in its complete isomerisation to 3m within 2
h.
(18) The reaction conditions were adopted from: Iovel, I.; Mertins, K.;
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́
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(8) (a) Kisi
̌ ́
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̌
́
(9) For reviews on DKR in ATH, see: (a) Pellissier, H. Tetrahedron
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̌
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