Supramolecular Photochirogenesis with
Cyclodextrin
18
Jiabin Yao, Yoshihisa Inoue, and Cheng Yang
Contents
18.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 509
18.2 CD-Mediated Unimolecular Photochirogenic Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 511
18.3 CD-Mediated Bimolecular Chiral Photochemical Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . 513
18.3.1 Enantiodifferentiating Photodimerization of Benzaldehyde Mediated
by Native β-CD . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 514
18.3.2 Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated
by Native and Modified γ-CD . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . 514
18.3.3 Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated
by β-CD via 2:2 Complex . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 517
18.3.4 Wavelength Control of Supramolecular Photochirogenesis
Mediated by CDs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 520
18.3.5 Dual Supramolecular Photocyclodimerization of 2-Anthracenecarboxylate
Anchored to α-CD Scaffold . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 522
18.3.6 Miscellaneous Bimolecular Chiral Photoreactions Mediated by CD . . . . . . . . . 524
18.4 Catalytic Supramolecular Photochirogenesis with Sensitizing CD Hosts . . . . . . . . . . . . . . 525
18.5 Conclusion and Future Perspective . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 530
18.6 Cross-References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 531
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 531
18.1 Introduction
Despite the recent success, asymmetric synthesis still remains some major challenges. In particular, chiral polycyclic and highly strained compounds are generally
difficult to obtain or tedious to prepare through conventional catalytic or enzymatic
J. Yao · C. Yang (*)
Sichuan University, Chengdu, China
e-mail: yangchengyc@scu.edu.cn
Y. Inoue (*)
Osaka University, Suita, Japan
e-mail: inoue@chem.eng.osaka-u.ac.jp
© Springer Nature Singapore Pte Ltd. 2020
Y. Liu et al. (eds.), Handbook of Macrocyclic Supramolecular Assembly,
https://doi.org/10.1007/978-981-15-2686-2_20
509
Cyclodextrin
18
Jiabin Yao, Yoshihisa Inoue, and Cheng Yang
Contents
18.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 509
18.2 CD-Mediated Unimolecular Photochirogenic Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 511
18.3 CD-Mediated Bimolecular Chiral Photochemical Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . 513
18.3.1 Enantiodifferentiating Photodimerization of Benzaldehyde Mediated
by Native β-CD . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 514
18.3.2 Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated
by Native and Modified γ-CD . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . 514
18.3.3 Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated
by β-CD via 2:2 Complex . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 517
18.3.4 Wavelength Control of Supramolecular Photochirogenesis
Mediated by CDs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 520
18.3.5 Dual Supramolecular Photocyclodimerization of 2-Anthracenecarboxylate
Anchored to α-CD Scaffold . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 522
18.3.6 Miscellaneous Bimolecular Chiral Photoreactions Mediated by CD . . . . . . . . . 524
18.4 Catalytic Supramolecular Photochirogenesis with Sensitizing CD Hosts . . . . . . . . . . . . . . 525
18.5 Conclusion and Future Perspective . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 530
18.6 Cross-References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 531
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 531
18.1 Introduction
Despite the recent success, asymmetric synthesis still remains some major challenges. In particular, chiral polycyclic and highly strained compounds are generally
difficult to obtain or tedious to prepare through conventional catalytic or enzymatic
J. Yao · C. Yang (*)
Sichuan University, Chengdu, China
e-mail: yangchengyc@scu.edu.cn
Y. Inoue (*)
Osaka University, Suita, Japan
e-mail: inoue@chem.eng.osaka-u.ac.jp
© Springer Nature Singapore Pte Ltd. 2020
Y. Liu et al. (eds.), Handbook of Macrocyclic Supramolecular Assembly,
https://doi.org/10.1007/978-981-15-2686-2_20
509