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10.1002/chem.202000010
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Chem. Soc. 2007, 129, 7730; d) T. Shibata, Y. Tahara, K. Tamura, K.
Endo, J. Am. Chem. Soc. 2008, 130, 3451; e) H. Sagae, K. Noguchi, M.
Hirano, K. Tanaka, Chem. Commun. 2008, 3804; f) T. Shibata, M.
Otomo, K. Endo, Synlett 2010, 8, 1235.
Eur. J. 2012, 18, 9225. c) H. Ueda, K. Masutomi, Y. Shibata, K. Tanaka,
Org. Lett. 2017, 19, 2913.
[19] For the structural determination for diastereomers 3hh and 3hh’, see
the Supporting Information.
[5]
For the rhodium-catalyzed asymmetric [2+2+2] cycloaddition using
acrylamides, see: a) M. Kobayashi, T. Suda, K. Noguchi, K. Tanaka,
Angew. Chem. Int. Ed. 2011, 50, 1664; Angew. Chem. 2011, 123,
1
702; b) J. Hara, M. Ishida, M. Kobayashi, K. Noguchi, K. Tanaka,
Angew. Chem. Int. Ed. 2014, 53, 2956; Angew. Chem. 2014, 126,
000; c) T. Yoshida, Y. Tajima, M. Kobayashi, K. Masutomi, K. Noguchi,
K. Tanaka, Angew. Chem. Int. Ed. 2015, 54, 8241; Angew. Chem. 2015,
27, 8359; d) S. Yoshizaki, Y. Nakamura, K. Masutomi, T. Yoshida, K.
3
1
Noguchi. Y. Shibata, K. Tanaka, Org. Lett. 2016, 18, 388.
[
6]
7]
K. Masutomi, N. Sakiyama, K. Noguchi, K. Tanaka, Angew. Chem. Int.
Ed. 2012, 51, 13031; Angew. Chem. 2012, 124, 13208.ꢀ
[
a) K. Masutomi, H. Sugiyama, H. Uekusa, Y. Shibata, K. Tanaka,
Angew. Chem. Int. Ed. 2016, 55, 15373; Angew. Chem. 2016, 128,
1
5599. For other examples of the rhodium-catalyzed asymmetric
2+2+2] cycloaddition using enamides, see: b) K. Tanaka, M. Takahashi,
H. Imase, T. Osaka, K. Noguchi, M. Hirano, Tetrahedron 2008, 64,
289; c) M. Kobayashi, T. Suda, K. Noguchi, K. Tanaka, Angew. Chem.
[
6
Int. Ed. 2011, 50, 1664; Angew. Chem. 2011, 123, 1702.
[
8]
9]
J. Ni, J. Chen, Y. Zhou, G. Wang, S. Li, Z. He, W. Sun, B. Fan, Adv.
Synth. Cat. 2019, 361, 3543.
[
Alternatively, in the nickel-catalyzed [2+2+2] cycloaddition, the use of
enones effectively suppresses the undesired β-hydrogen elimination.
See: a) J. Seo, H. M. P. Chui, M. J. Heeg, J. Montgomery, J. Am. Chem.
Soc. 1999, 121, 476; b) S. Ogoshi, A. Nishimura, M. Ohashi, Org. Lett.
2010, 12, 3450; c) R. Kumar, H. Tokura, A. Nishimura, T. Mori, Y.
Hoshimoto, M. Ohashi, S. Ogoshi. Org. Lett. 2015, 17, 6018.
[
10] The rhodium(I)-catalyzed asymmetric cycloisomerization of 1,6-enynes,
possessing a racemic secondary alcohol moiety, to produce chiral
ketones was reported. See: Y. Oonishi, S. Masusaki, S. Sakamoto, Y.
Sato, Angew. Chem. Int. Ed. 2019, 58, 8736; Angew. Chem. 2019, 131,
8828.
[
11] For the transition-metal-catalyzed C-C bond forming reactions involving
the kinetic resolution of allylic alcohols, see: a) Y. Wang, X. Feng, H.
Du, Org. Lett. 2011, 13, 4954. b) F. Wang, S. Li, M. Qu, M.-X. Zhao, L.-
J. Liu, M. Shi, Chem. Commun. 2011, 47, 12813. c) S.-B. Tang, X.
Zhang, H.-F. Tu, S.-L. You, J. Am. Chem. Soc. 2018, 140, 7737.
[
[
[
12] M. Fernández, M. Parena, T. Parella, A. Lledó, J. L. Bras, J. Muzart, A.
Pla-Quintana, A. Roglans, Adv. Synth. Catal. 2016, 358. 1848.ꢀ
13] For a review , see: H. Shimizu, I. Nagasaki, T. Saito, Tetrahedron 2005,
61, 5405.ꢀ
14] CCDC 1971249 [(+)-3aa] contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge from The
Cambridge
www.ccdc.cam.ac.uk/data_request/cif.
15] The rhodium-catalyzed enantioselective
Crystallographic
Data
Centre
via
[
stereoconvergent
isomerization of racemic secondary homoallylic and bishomoallylic
alcohols was reported. See: R.-Z. Huang, K. K. Lau, Z. Li, T.-L. Liu, Y.
Zhao, J. Am. Chem. Soc. 2018, 140, 14647.ꢀ
[
16] For the rhodium-catalyzed kinetic resolution of racemic secondary
allylic alcohols through the olefin isomerization, see: a) K. Ohkubo, T.
Ohgushi, T. Kusaga, K. Yoshinaga, Inorg. Nucl. Chem. Lett. 1977, 13,
631. b) M. Kitamura, K. Manabe, R. Noyori, H. Takaya, Tetrahedron
Lett. 1987, 28, 4719. c) K. Ren, L. Zhang, B. Hu, M. Zhao, Y. Tu, X. Xie,
T. Y. Zhang, Z. Zhang, ChemCatChem 2013, 5, 1317; d) K. Ren, M.
Zhao, B. Hu, B. Lu, X. Xie, V. Ratovelomanana-Vidal, Z. Zhang, J. Org.
Chem. 2015, 80, 12572. The rhodium-catalyzed enantioselective
stereoconvergent isomerization of racemic secondary allylic alcohols
was also reported. See: e) T.-L. Liu, T. W. Ng, Y. Zhao, J. Am. Chem.
Soc. 2017, 139, 3643.
[
17] In the reactions shown in Scheme 2, secondary allylic alcohols, which
did not react with 1,6-enynes, were converted to a complex mixture of
products presumably through the olefin isomerization. Therefore, the
selectivity factor could not be determined.
[
18] For examples of β-Hydride elimination from seven-membered
rhodacycles, see: a) M. Ishida, Y. Shibata, K. Noguchi, K. Tanaka,
Chem. Eur. J. 2011, 17, 12578; b) M. Kobayashi, K. Tanaka, Chem.
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