Skip to main content
Top
Published in:
Cover of the book

2015 | Online First | Chapter

Brønsted Acid/Lewis Base Hybrid Complexes

Authors : Manabu Hatano, Kazuaki Ishihara

Published in: Topics in Organometallic Chemistry

Publisher: Springer International Publishing

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Recent progress on our Brønsted acid/Lewis base hybrid complexes in some asymmetric catalyses is reviewed. Based on the rational design of conjugated acid–base catalysts, tailor-made supramolecular catalysts can show remarkable catalytic activity and higher-ordered selectivities that cannot be realized by ready-made single-molecule catalysts. The chiral supramolecular magnesium(II) binaphtholate complexes trigger the highly enantioselective 1,4-hydrophosphinylation and 1,2-hydrophosphonylation of α,β-unsaturated carbonyl compounds, direct Mannich-type reaction, and hetero-Diels–Alder reaction. Moreover, the advanced supramolecular catalysts are prepared in situ from chiral 3,3′-disubstituted binaphthols and biphenols, arylboronic acid, and B(C6F5)3, for promoting the anomalous endo-/exo-selective Diels–Alder reaction. The specific mechanism and deep insights into the possible key intermediates are discussed on the basis of rational design of chiral supramolecular Brønsted acid/Lewis base hybrid catalysts as artificial enzymes.
Literature
5.
6.
9.
go back to reference Tanaka K, Kukita K, Ichibakase T, Kotani S, Nakajima M (2011) Chem Commun 47:5614CrossRef Tanaka K, Kukita K, Ichibakase T, Kotani S, Nakajima M (2011) Chem Commun 47:5614CrossRef
10.
go back to reference Kotani S, Kukita K, Tanaka K, Ichibakase T, Nakajima M (2014) J Org Chem 79:4817CrossRef Kotani S, Kukita K, Tanaka K, Ichibakase T, Nakajima M (2014) J Org Chem 79:4817CrossRef
13.
go back to reference Du H, Zhang X, Wang Z, Bao H, You T, Ding K (2008) Eur J Org Chem 2248 Du H, Zhang X, Wang Z, Bao H, You T, Ding K (2008) Eur J Org Chem 2248
16.
18.
19.
20.
24.
27.
34.
go back to reference Enders D, Saint-Dizier A, Lannou MI, Lenzen A (2006) Eur J Org Chem 2006:29CrossRef Enders D, Saint-Dizier A, Lannou MI, Lenzen A (2006) Eur J Org Chem 2006:29CrossRef
35.
37.
go back to reference Zhou X, Liu Y, Chang L, Zhao J, Shang D, Liu X, Lin L, Feng X (2009) Adv Synth Catal 351:2567CrossRef Zhou X, Liu Y, Chang L, Zhao J, Shang D, Liu X, Lin L, Feng X (2009) Adv Synth Catal 351:2567CrossRef
39.
go back to reference Zhou X, Zhang Q, Hui Y, Chen W, Jiang J, Lin L, Liu X, Feng X (2010) Org Lett 12:4296CrossRef Zhou X, Zhang Q, Hui Y, Chen W, Jiang J, Lin L, Liu X, Feng X (2010) Org Lett 12:4296CrossRef
40.
41.
42.
go back to reference Gröger H, Saida Y, Arai S, Martens J, Sasai H, Shibasaki M (1996) Tetrahedron Lett 37:9291CrossRef Gröger H, Saida Y, Arai S, Martens J, Sasai H, Shibasaki M (1996) Tetrahedron Lett 37:9291CrossRef
43.
44.
go back to reference Gröger H, Saida Y, Sasai H, Yamaguchi K, Martens J, Shibasaki M (1998) J Am Chem Soc 120:3089CrossRef Gröger H, Saida Y, Sasai H, Yamaguchi K, Martens J, Shibasaki M (1998) J Am Chem Soc 120:3089CrossRef
45.
go back to reference Schlemminger I, Saida Y, Gröger H, Maison W, Durot N, Sasai H, Shibasaki M, Martens J (2000) J Org Chem 65:4818CrossRef Schlemminger I, Saida Y, Gröger H, Maison W, Durot N, Sasai H, Shibasaki M, Martens J (2000) J Org Chem 65:4818CrossRef
46.
go back to reference Mastryukova TA, Aladzheva IM, Leont’eva IV, Petrovski PV, Fedin EI, Kabachnik MI (1980) Pure Appl Chem 52:945CrossRef Mastryukova TA, Aladzheva IM, Leont’eva IV, Petrovski PV, Fedin EI, Kabachnik MI (1980) Pure Appl Chem 52:945CrossRef
48.
49.
go back to reference Sekine M, Nakajima M, Kume A, Hashizume A, Hata T (1982) Bull Chem Soc Jpn 55:224CrossRef Sekine M, Nakajima M, Kume A, Hashizume A, Hata T (1982) Bull Chem Soc Jpn 55:224CrossRef
51.
54.
55.
58.
60.
68.
go back to reference Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G (2002) Angew Chem Int Ed 41:1668CrossRef Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G (2002) Angew Chem Int Ed 41:1668CrossRef
69.
70.
go back to reference Du H, Ding K (2010) In: Ma S (ed) Handbook of cyclization reactions. Wiley-VCH, Stuttgart, pp 1–57 Du H, Ding K (2010) In: Ma S (ed) Handbook of cyclization reactions. Wiley-VCH, Stuttgart, pp 1–57
71.
go back to reference Ishihara K, Sakakura A (2011) In: Evans PA (ed) Science of synthesis, stereoselective synthesis, vol 3. Thieme, Weinheim, pp 67–123 Ishihara K, Sakakura A (2011) In: Evans PA (ed) Science of synthesis, stereoselective synthesis, vol 3. Thieme, Weinheim, pp 67–123
73.
74.
go back to reference Barba C, Carmona D, García JI, Lamata MP, Mayoral JA, Salvatella L, Viguri F (2006) J Org Chem 71:9831CrossRef Barba C, Carmona D, García JI, Lamata MP, Mayoral JA, Salvatella L, Viguri F (2006) J Org Chem 71:9831CrossRef
75.
go back to reference Wannere CS, Paul A, Herges R, Houk KN, Schaefer HF III, von Ragué SP (2007) J Comp Chem 28:344CrossRef Wannere CS, Paul A, Herges R, Houk KN, Schaefer HF III, von Ragué SP (2007) J Comp Chem 28:344CrossRef
77.
go back to reference Kündig EP, Saudan CM, Alezra V, Viton F, Bernardinelli G (2001) Angew Chem Int Ed 40:4481CrossRef Kündig EP, Saudan CM, Alezra V, Viton F, Bernardinelli G (2001) Angew Chem Int Ed 40:4481CrossRef
78.
go back to reference Sibi MP, Nie X, Shackleford JP, Stanley LM, Bouret F (2008) Synlett 2008:2655CrossRef Sibi MP, Nie X, Shackleford JP, Stanley LM, Bouret F (2008) Synlett 2008:2655CrossRef
81.
82.
83.
go back to reference Takamura M, Hamashima Y, Usuda H, Kanai M, Shibasaki M (2000) Angew Chem Int Ed 39:1650CrossRef Takamura M, Hamashima Y, Usuda H, Kanai M, Shibasaki M (2000) Angew Chem Int Ed 39:1650CrossRef
84.
85.
go back to reference Takamura M, Funabashi K, Kanai M, Shibasaki M (2000) J Am Chem Soc 122:6327CrossRef Takamura M, Funabashi K, Kanai M, Shibasaki M (2000) J Am Chem Soc 122:6327CrossRef
86.
87.
88.
go back to reference Morimoto H, Yoshino T, Yukawa T, Lu G, Matsunaga S, Shibasaki M (2008) Angew Chem Int Ed 47:9125CrossRef Morimoto H, Yoshino T, Yukawa T, Lu G, Matsunaga S, Shibasaki M (2008) Angew Chem Int Ed 47:9125CrossRef
89.
go back to reference Yamatsugu K, Yin L, Kamijo S, Kimura Y, Kanai M, Shibasaki M (2009) Angew Chem Int Ed 48:1070CrossRef Yamatsugu K, Yin L, Kamijo S, Kimura Y, Kanai M, Shibasaki M (2009) Angew Chem Int Ed 48:1070CrossRef
91.
93.
go back to reference Yanagida Y, Yazaki R, Kumagai N, Shibasaki M (2011) Angew Chem Int Ed 50:7910CrossRef Yanagida Y, Yazaki R, Kumagai N, Shibasaki M (2011) Angew Chem Int Ed 50:7910CrossRef
94.
101.
go back to reference Hatano M, Gouzu R, Mizuno T, Abe H, Yamada T, Ishihara K (2011) Catal Sci Technol 1:1149CrossRef Hatano M, Gouzu R, Mizuno T, Abe H, Yamada T, Ishihara K (2011) Catal Sci Technol 1:1149CrossRef
102.
go back to reference Hatano M, Mizuno T, Izumiseki A, Usami R, Asai T, Akakura M, Ishihara K (2011) Angew Chem Int Ed 50:12189CrossRef Hatano M, Mizuno T, Izumiseki A, Usami R, Asai T, Akakura M, Ishihara K (2011) Angew Chem Int Ed 50:12189CrossRef
104.
go back to reference Ishihara K, Kurihara H, Matsumoto M, Yamamoto H (1998) J Am Chem Soc 120:6920CrossRef Ishihara K, Kurihara H, Matsumoto M, Yamamoto H (1998) J Am Chem Soc 120:6920CrossRef
105.
go back to reference Beckett MA, Brassington DS, Light ME, Hursthouse MB (2001) J Chem Soc Dalton Trans 2001:1768CrossRef Beckett MA, Brassington DS, Light ME, Hursthouse MB (2001) J Chem Soc Dalton Trans 2001:1768CrossRef
106.
Metadata
Title
Brønsted Acid/Lewis Base Hybrid Complexes
Authors
Manabu Hatano
Kazuaki Ishihara
Copyright Year
2015
Publisher
Springer International Publishing
DOI
https://doi.org/10.1007/3418_2015_143