Keywords
aldehydes
alkylation
allylboration
asymmetric autoamplification
autocatalysis
diisopropylzinc
Soai reaction
spontaneous generation of chirality
Abstract
Analysis of the available data on the Soai reaction, including the most recent experimental and computational findings, allowed us to conclude that an asymmetric autocatalytic amplification (AAA) takes place only when both the monomer and the smallest possible oligomer (dimer) of the product/catalyst are catalytically non-competent.
Funders
Russian Science Foundation
22-13-00275-P
References
1.
Soai K., Shibata T., Morioka H., Choji K.
Nature,
1995
3.
Buhse T., Cruz J., Noble-Terán M.E., Hochberg D., Ribó J.M., Crusats J., Micheau J.
Chemical Reviews,
2021
4.
Singleton D.A., Vo L.K.
Organic Letters,
2003
5.
Soai K., Sato I., Shibata T., Komiya S., Hayashi M., Matsueda Y., Imamura H., Hayase T., Morioka H., Tabira H., Yamamoto J., Kowata Y.
Tetrahedron Asymmetry,
2003
6.
Gridnev I.D., Serafimov J.M., Quiney H., Brown J.M.
Organic and Biomolecular Chemistry,
2003
7.
Mikhaylov O.A., Saigitbatalova E.S., Latypova L.Z., Kurbangalieva A.R., Gridnev I.D.
Symmetry,
2023
8.
Mikhailov O.A., Gurskii M.E., Kurbangalieva A.R., Gridnev I.D.
International Journal of Molecular Sciences,
2024
9.
Mikhailov O., Gridnev I.D.
Molecules,
2025
10.
Sato I., Yanagi T., Soai K.
Chirality,
2002
11.
Shibata T., Morioka H., Hayase T., Choji K., Soai K.
Journal of the American Chemical Society,
1996
12.
Sato I., Urabe H., Ishiguro S., Shibata T., Soai K.
Angewandte Chemie - International Edition,
2003
13.
Kawasaki T., Nakaoda M., Takahashi Y., Kanto Y., Kuruhara N., Hosoi K., Sato I., Matsumoto A., Soai K.
Angewandte Chemie,
2014
14.
Kawasaki T., Ishikawa Y., Minato Y., Otsuka T., Yonekubo S., Sato I., Shibata T., Matsumoto A., Soai K.
Chemistry - A European Journal,
2016
15.
Sato I., Urabe H., Ishii S., Tanji S., Soai K.
Organic Letters,
2001
16.
Kaur J., Barham J.P.
Chemistry - A European Journal,
2025
17.
10.1002/(SICI)1521-3773(19981116)37:21\%3C2922::AID-ANIE2922\%3E3.0.CO;2-1
18.
Frank F.C.
Biochimica et Biophysica Acta - General Subjects,
1953
19.
Blackmond D.G.
Chemical Reviews,
2019
20.
Gridnev I.D., Serafimov J.M., Brown J.M.
Angewandte Chemie,
2004
21.
Gridnev I.D., Brown J.M.
Proceedings of the National Academy of Sciences of the United States of America,
2004
22.
Gridnev I.D., Vorobiev A.K.
ACS Catalysis,
2012
23.
Brown J.M., Gridnev I., Klankermayer J.
Topics in Current Chemistry,
2008
24.
Matsumoto A., Abe T., Hara A., Tobita T., Sasagawa T., Kawasaki T., Soai K.
Angewandte Chemie - International Edition,
2015
25.
Schiaffino L., Ercolani G.
Angewandte Chemie - International Edition,
2008
26.
Schiaffino L., Ercolani G.
ChemPhysChem,
2009
27.
Schiaffino L., Ercolani G.
Chemistry - A European Journal,
2010
28.
Ercolani G., Schiaffino L.
Journal of Organic Chemistry,
2011