Green Chemistry
Communication
revealed the existence of the reverse catalytic cycle. The syn-
thetic utility of the system was documented by the formal con-
tinuous-flow synthesis of chiral fenpentadiol analogue 4. This
flow system is anticipated to become an important component
of modular organic synthesis to access natural products, bio-
active molecules, and materials.
(b) A. L. Handlon, L. T. Schaller, L. M. Leesnitzer,
R. V. Merrihew, C. Poole, J. C. Ulrich, J. H. W. Wilson,
R. Cadilla and P. Turnbull, ACS Med. Chem. Lett., 2016, 7,
83; (c) J. W. Lee, M. T. Oliveira, H. B. Jang, S. Lee, D. Y. Chi,
D. W. Kim and C. E. Song, Chem. Soc. Rev., 2016, 45, 4638;
(d) J. Nie, H. C. Guo, D. Cahard and J. A. Ma, Chem. Rev.,
2011, 111, 455–529; (e) S. Purser, P. Moore, S. Swallow and
V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320–330.
Conflicts of interest
6 (a) P. Melchiorre, M. Marigo, A. Carlone and G. Bartoli,
Angew. Chem., Int. Ed., 2008, 47, 6138; (b) B. M. Trost and
C. S. Brindle, Chem. Soc. Rev., 2010, 39, 1600.
There are no conflicts to declare.
7 (a) N. Hara, R. Tamura, Y. Funahashi and S. Nakamura,
Org. Lett., 2011, 13, 1662; (b) N. Duangdee, W. Harnying,
G. Rulli, J. M. Neudorfl, H. Groger and A. Berkessel, J. Am.
Chem. Soc., 2012, 134, 11196; (c) J. T. Guo, Y. Xiang,
Z. Guan and Y. H. He, J. Mol. Catal. B: Enzym., 2016, 131,
55; (d) C. G. Kokotos, J. Org. Chem., 2012, 77, 1131;
(e) S. Zhang, L. Li, Y. Hu, Y. Li, Y. Yang, Z. Zha and
Z. Wang, Org. Lett., 2015, 17, 5036; (f) H. Zong,
H. Y. Huang, G. L. Bian and L. Song, J. Org. Chem., 2014,
79, 11768; (g) I. Vlasserou, M. Sfetsa, D. T. Gerokonstantis,
C. G. Kokotos and P. Mountevelis-Minakakis, Tetrahedron,
2018, 74, 2338; (h) X. Y. Meng, Y. Y. Luo and G. Zhao,
Tetrahedron Lett., 2002, 61, 152485.
8 (a) B. Gutmann, D. Cantillo and C. O. Kappe, Angew.
Chem., Int. Ed., 2015, 54, 6688; (b) G. Jas and A. Kirschning,
Chem. – Eur. J., 2003, 9, 5708; (c) S. Kobayashi, Chem. –
Asian J., 2016, 11, 425; (d) D. Webb and T. F. Jamison,
Chem. Sci., 2010, 1, 675.
9 For possible catalyst deactivation pathways in the aminoca-
talysis, see: (a) D. E. Siyutkin, A. S. Kucherenko and
S. G. Zlotin, Tetrahedron, 2010, 66, 513; (b) O. V. Maltsev,
A. O. Chizhov and S. G. Zlotin, Chem. – Eur. J., 2011, 17,
6109.
Acknowledgements
This work was partially supported by the Japan Agency for
Medical Research and Development (AMED) (S. K.) and by the
Japan Society for the Promotion of Science (JSPS) KAKENHI
(Grant No. JP 17H06448) (Y. Y.).
Notes and references
1 (a) C. F. Barbas III, Angew. Chem., Int. Ed., 2008, 47, 42;
(b) P. M. Pihko, Angew. Chem., Int. Ed., 2004, 43, 2062;
(c) P. R. Schreiner, Chem. Soc. Rev., 2003, 32, 289;
(d) K. A. Ahrendt, C. J. Borths and D. W. C. MacMillan,
J. Am. Chem. Soc., 2000, 122, 4243.
2 (a) K. Ding and Y. Uozumi, Handbook of Asymmetric
Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2008;
(b) M. Gruttadauria, F. Giacalone and R. Noto, Chem. Soc.
Rev., 2008, 37, 1666.
3 (a) Y. Li, X. Y. Liu and G. Zhao, Tetrahedron: Asymmetry,
2006, 17, 2034; (b) M. C. Varela, S. M. Dixon, K. S. Lam and
N. E. Schore, Tetrahedron, 2008, 64, 10087; (c) I. Mager and
K. Zeitler, Org. Lett., 2010, 12, 1480; (d) W. Zheng, C. Lu, 10 (a) M. R. Vishnumaya, S. K. Ginotra and V. K. Singh, Org.
G. Yang, Z. Chen and J. Nie, Catal. Commun., 2015, 62, 34;
(e) M. Gruttadauria, F. Giacalone, A. M. Marculescu and
R. Noto, Adv. Synth. Catal., 2008, 350, 1397; (f) G. Rulli,
K. A. Fredriksen, N. Duangdee, T. Bonge-Hansen,
A. Berkessel and H. Gröger, Synthesis, 2013, 45, 2512.
4 (a) E. Alza, C. Rodríguez-Escrich, S. Sayalero, A. Bastero and
M. A. Pericàs, Chem. – Eur. J., 2009, 15, 10167; (b) X. Fan,
S. Sayalero, C. Rodríguez-Escrich and M. A. Pericàs, Adv.
Synth. Catal., 2012, 354, 2971; (c) P. Llanes, C. Rodríguez-
Escrich, S. Sayalero and M. A. Pericàs, Org. Lett., 2016, 18,
6292–6295; (d) R. Martín-Rapún, S. Sayalero and
Lett., 2006, 8, 4097; (b) V. Maya, M. Raj and V. K. Singh,
Org. Lett., 2007, 9, 2593; (c) M. Raj, V. Maya and
V. K. Singh, J. Org. Chem., 2009, 74, 4289; (d) M. Raj and
V. K. Singh, Chem. Commun., 2009, 6687.
11 (a) T. Tsubogo, H. Oyamada and S. Kobayashi, Nature,
2015, 520, 329; (b) S. Kobayashi, M. Okumura, Y. Akatsuka,
H. Miyamura, M. Ueno and H. Oyamada, ChemCatChem,
2015, 7, 4025; (c) H. Ishitani, Y. Saito, T. Tsubogo and
S. Kobayashi, Org. Lett., 2016, 18, 1346; (d) P. Borah,
Y. Yamashita and S. Kobayashi, Angew. Chem. Int. Ed., 2017,
56, 10330.
M. A. Pericàs, Green Chem., 2013, 15, 3295; 12 Different from previous examples, the emerging diastereo-
(e) I. Sagamanova, C. Rodríguez-Escrich, I. G. Molnár,
S. Sayalero, R. Gilmour and M. A. Pericàs, ACS Catal., 2015,
5, 6241; (f) C. De Risi, O. Bortolini, A. Brandolese, G. Di
mers had a significant impact on the H-bonding inter-
action of OH and the carbonyl group, leading to decreased
enantioselectivity.
Carmine, D. Ragno and A. Massi, React. Chem. Eng., 2020, 13 The absolute configuration of 3a was confirmed by the ana-
5, 1017. lysis of our HPLC data and previously reported data.
5 (a) Y. Ducharme, M. Blouin, C. Brideau, A. Châteauneuf, 14 (a) K. Patora-Komisarska, M. Benohoud, H. Ishikawa,
Y. Gareau, E. L. Grimm, H. Juteau, S. Laliberté, B. MacKay,
F. Massé, M. Ouellet, M. Salem, A. Styhler and
R. W. Friesen, ACS Med. Chem. Lett., 2010, 1, 170;
D. Seebach and Y. Hayashi, Helv. Chim. Acta, 2011, 94, 719;
(b) J. Burés, A. Armstrong and D. G. Blackmond, J. Am.
Chem. Soc., 2011, 133, 8822.
This journal is © The Royal Society of Chemistry 2021
Green Chem., 2021, 23, 1989–1994 | 1993