10.1002/anie.202004797
Angewandte Chemie International Edition
COMMUNICATION
6482-6484; d) G. Balavoine, S. Juge, H. B. Kagan, Tetrahedron Lett.
1973, 14, 4159-4162.
J. Am. Chem. Soc. 2013, 135, 4970-4973. c) J. S. Barber, M. M. Yamano,
M. Ramirez, E. R. Darzi, R. R. Knapp, F. Liu, K. N. Houk, N. K. Garg,
Nat. Chem. 2018, 10, 953-960.
[5]
Recent reviews: a) Q. Shi, J. Ye, Angew. Chem. 2020, 132, 5030-5033;
Angew. Chem. Int. Ed. 2020, 59, 4998-5001; b) b) C. Yang, Y. Inoue,
Nature 2018, 564, 197-199.
[16] For reviews on general axial-to-point chirality transfer employing allenes,
see: a) S. Ma, Chem. Soc. Rev. 2005, 105, 2829-2871; b) D. Campolo,
S. Gastaldi, C. Roussel, M. P. Betrand, M. Nechab, Chem. Soc. Rev.
2013, 42, 8434-8466; c) J. M. Alonso, M. T. Quirós, M. P. Muñoz, Org.
Chem. Front. 2016, 3, 1186-1204.
[6]
[7]
a) A. Hölzl-Hobmeier, A. Bauer, A. V. Silva, S. M. Huber, C. Bannwarth,
T. Bach, Nature 2018, 564, 240-243.
a) A. Tröster, A. Bauer, C. Jandl, T. Bach, Angew. Chem. 2019, 131,
3576-3579; Angew. Chem. Int. Ed. 2019, 58, 3538-3541; b) L.
Wimberger, T. Kratz, T. Bach, Synthesis 2019, 51, 4417-4424.
N. Y. Shin, J. M. Ryss, X. Zhang, S. J. Miller, R. R. Knowles, Science
2019, 366, 364-369.
[17] For key references to photochemical axial-to-point chirality transfer, see:
a) A. J.-L. Ayitou, J. L. Jesuraj, N. Barooah, A. Ugrinov, J. Sivaguru, J.
Am. Chem. Soc. 2009, 131, 11314-11315; b) E. Kumarasamy, A. J.-L.
Ayitou, N. Vallavoju, R. Raghunathan, A. Iyer, A. Clay, S. K. Kandappa,
J. Sivaguru, Acc. Chem. Res. 2016, 49, 2713-2724.
[8]
[9]
For a recent review on reactions mediated by triplet energy transfer, see:
Q.-Q. Zhou, Y.-Q. Zou, L.-Q. Lu, W.-J. Xiao, Angew. Chem. 2019, 131,
1600-1619; Angew. Chem. Int. Ed. 2019, 58, 1586-1604.
[18] Supplementary crystallographic data for 5a have been deposited with the
Cambridge Crystallographic Data Centre (CCDC 1988993).
[19] For examples of a chirality transfer in Diels-Alder reactions of trisub-
stituted allenes with an electron withdrawing group, see: a) J. Yu, W.-J.
Chen, L.-Z. Gong, Org. Lett. 2010, 12, 4050-5053; b) Z.-G. Ma, J.-L. Wei,
J.-B. Lin, G.-J. Wang, J. Zhou, K. Chen, C.-A. Fan, S.-Y. Zhang, Org.
Lett. 2019, 21, 2468-2472.
[10] For the synthesis of enantiomerically enriched allenes and their use in
organic synthesis, see: a) N. Krause, A. S. K. Hashmi, Modern Allene
Chemistry, Wiley-VCH, Weinheim, 2004; b) S. Yu, S. Ma, Angew. Chem.
2012, 124, 3128-3167; Angew. Chem. Int. Ed. 2012, 51, 3074-3112; c)
W. Chu, Y. Zhang, J. Wang, Catal. Sci. Technol. 2017, 7, 4570-4579; d)
X. Huang, S. Ma, Acc. Chem. Res. 2019, 52, 1301-1312.
[20] V. M. Marx, T. S. Cameron, D. J. Burnell. Tetrahedron Lett. 2009, 50,
7213-7216.
[11] a) H. Gotthardt, G. S. Hammond, Chem. Ber. 1975, 108, 657-663; b) J.
Kamphuis, H. J. T. Bos, R. J. Visser, B. H. Huizer, C. A. G. O. Varma, J.
Chem. Soc., Perkin Trans. 2. 1986, 1867-1874; c) T. Tsuno, H. Hoshino,
K. Sugiyama. Tetrahedron Lett. 1997, 38, 1581-1584; d) B. Alcaide, P.
Almendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783-816.
[12] A. Iyer, A. Clay, S. Jockusch, J. Sivaguru, J. Phys. Org. Chem. 2017, 30,
e3738.
[21] L. R. Byrd, M. C. Caserio, J. Am. Chem. Soc. 1971, 93, 5758-5764.
[22] W. Smadja, Chem. Rev. 1983, 83, 263-320.
[23] a) G.-L. Zhao, J. W. Huang, M. Shi, Org. Lett. 2003, 5, 4737-4739; b) G.
Rassu, V. Zambrano, R. Tanca, A. Sartori, L. Battistini, F. Zanardi, C.
Curti, G. Casiraghi, Eur. J. Org. Chem. 2012, 466-470; d) F. Manoni, S.
J. Connon, Angew. Chem. 2014, 126, 2666-2670; Angew. Chem. Int. Ed.
2014, 53, 2628-2632.
[13] a) P. Kapitán, T. Bach, Synthesis 2008, 1559-1564; b) D. Lenhart, A.
Bauer, A. Pöthig, T. Bach, Chem. Eur. J. 2016, 22, 6519-6523; (c) For a
review on hydrogen bonding to this core, see: F. Burg, T. Bach, J. Org.
Chem. 2019, 84, 8815-8836.
[24] C. Chen, P. Kattanguru, O. A. Tomashenko, R. Karpowicz, G.
Siemiaszko, A. Bhattacharya, V. Calasans, Y. Six, Org. Biomol. Chem.
2017, 15, 5364-5372.
[14] For a related sensitizer that operates by hydrogen bonding, see: K. L.
Skubi, J. B. Kidd, H. Jung, I. A. Guzei, M.-H. Baik, T. P. Yoon, J. Am.
Chem. Soc. 2017, 139, 17186-17192.
[25] R. Alonso, T. Bach, Angew. Chem. 2014, 126, 4457-4460; Angew.
Chem. Int. Ed. 2014, 53, 4368-4371.
[15] Examples of Diels-Alder reactions with electron-deficient allenes: a) H.
Kimura, T. Fujiwara, T. Katoh, K. Nishide, T. Kajimoto, M. Node, Chem.
Pharm. Bull. 2006, 54, 399-402. b) I. T. Crouch, R. K. Neff, D. E. Frantz,
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