[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2007.28.12.2162

Selective Reduction of Carbonyl and Epoxy Compounds Using Aluminum, Boron and Other Metal Reagents. Comparison of Reducing Characteristics between the Meerwein-Ponndorf-Verley Type Reduction and Metal Complex Hydrides Reduction: A Review

Cha, Jin-Soon (Department of Chemistry, Yeungnam University)

Publication Information

Bulletin of the Korean Chemical Society / v.28, no.12, 2007 , pp. 2162-2190 More about this Journal

Abstract

The newly-developed Meerwein-Ponndorf-Verley (MVP) type reagents using aluminum, boron and other metals for reduction of organic functional groups such as carbonyl and epoxy compounds have been surveyed. highlighted and reviewed in this account are the appearance of new MPV type reagents and their application to the selective reduction of organic functions. Finally, this account emphasizes the distinct contrast in the reducing characteristics existed between metal hydride reagents and MPV reagents, and compares their usefulness in organic synthesis.

Keywords

Metal complex hydrides; MPV reactions; Reduction; Carbonyl and epoxy compounds; Aluminum and boron reagents;

Citations & Related Records

Times Cited By KSCI : 9 (Citation Analysis)
Times Cited By Web Of Science : 14 (Related Records In Web of Science)
Times Cited By SCOPUS : 3

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Reference
Cited By KSCI
Cited By SCOPUS

1	Reaction of Sodium Cyanoaluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups / [Cha, Jin-Soon;Yu, Se-Jin;Roh, Min-Young;Yi, Ja-Eun;Park, Seung-Jin;Kwon, Oh-Oun;] / Bulletin of the Korean Chemical Society
2	Regioselective Cleavage of Phenyl- or Alkyl-Substituted Epoxides with Al-Fluorodiisobutylalane / [Cha, Jin-Soon;Park, Seung-Jin;Yu, Se-Jin;Kim, Seung-Kook;Kwon, Oh-Oun;] / Bulletin of the Korean Chemical Society
3	Reaction of Aldehydes and Ketones with Dichloroisopropoxyborane. Comparison of the Reducing Characteristics of Isopropoxyborane Derivatives / [Cha, Jin-Soon;Yu, Se-Jin;Roh, Min-Young;Park, Seung-Jin;Yi, Ja-Eun;Kwon, Oh-Oun;] / Bulletin of the Korean Chemical Society
4	Relative Reactivity of Various Al-substituted-dialkylalans in Reduction of Carbonyl Compounds: A Theoretical Study on Substituent Effect / [Nahm, Keepyung;Cha, Jin Soon;] / Bulletin of the Korean Chemical Society
5	Selective Reduction of Carbonyl Compounds with B-Trifluoromethanesulfonyldiisopinocampheylborane in Ethyl Ether / [Cha, Jin-Soon;] / Bulletin of the Korean Chemical Society
6	Regioselective Ring Cleavage of Phenyl- or/and Alkyl- Substituted Epoxides with Al-Methanesulfonyldiisobutylalane / [Cha, Jin-Soon;Park, Seung-Jin;] / Bulletin of the Korean Chemical Society
7	Regioselective Ring Cleavage of Phenyl- or/and Alkyl-Substituted Epoxides with Al-Trifluoromethanesulfonyldiisobutylalane. Comparison of Its Reactivity with Al-Methanesulfonyldiisobutylalane / [Cha, Jin-Soon;Park, Seung-Jin;] / Bulletin of the Korean Chemical Society
8	Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane / [Cha, Jin-Soon;Noh, Min-Yeong;] / Bulletin of the Korean Chemical Society
9	Thirty Six Years of Research on the Selective Reduction and Hydroboration / [Cha, Jin-Soon;] / Bulletin of the Korean Chemical Society
10	Selective Reduction of Organic Compounds with Al-Trifluoromethanesulfonyldiisobutylalane. Comparison of Its Reactivity with Al-Methanesulfonyldiisobutylalane / [Cha, Jin-Soon;] / Bulletin of the Korean Chemical Society
11	MPV-Reduction of C=O bond with Al-substituted-dialkylalan; A Theoretical Study on Relative Reactivity of Various Carbonyl Substrates / [Nahm, Keepyung;] / Bulletin of the Korean Chemical Society

6	Jin-Soon Cha. (2011) Bulletin of the Korean Chemical Society Thirty Six Years of Research on the Selective Reduction and Hydroboration / 32 (6) , 1808
14	Weiliang Xu. (2012) RSC Advances Calcium amidoborane, a new reagent for chemoselective reduction of α,β-unsaturated aldehydes and ketones to allylic alcohols / 2 (14) , 6005
8	Keepyung Nahm. (2013) Bulletin of the Korean Chemical Society Relative Reactivity of Various Al-substituted-dialkylalans in Reduction of Carbonyl Compounds: A Theoretical Study on Substituent Effect / 34 (8) , 2335
12	L. Grazia. (2016) Catal. Sci. Technol. Gas-phase cascade upgrading of furfural to 2-methylfuran using methanol as a H-transfer reactant and MgO based catalysts / 6 (12) , 4418
15	Jin Soon Cha. (2008) ChemInform ChemInform Abstract: Selective Reduction of Carbonyl and Epoxy Compounds Using Aluminum, Boron and Other Metal Reagents. Comparison of Reducing Characteristics Between the Meerwein-Ponndorf-Verley Type Reduction and Metal Complex Hydrides Reduction: A Review / 39 (15)
7	(2009) Bulletin of the Korean Chemical Society Selective Reduction of Carbonyl Compounds with B-Trifluoromethanesulfonyldiisopinocampheylborane in Ethyl Ether / 30 (7) , 1658
1-2	Jin Soon Cha. (2009) Journal of Inclusion Phenomena and Macrocyclic Chemistry Reaction of lithium tris(tert-butylthiolato)hydridoaluminate with selected organic compounds containing representative functional groups / 65 (1-2) , 7
12	(2007) Bulletin of the Korean Chemical Society Reaction of Sodium Cyanoaluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups / 29 (12) , 2379
2	(2007) Bulletin of the Korean Chemical Society Regioselective Cleavage of Phenyl- or Alkyl-Substituted Epoxides with Al-Fluorodiisobutylalane / 29 (2) , 301
4	(2007) Bulletin of the Korean Chemical Society Reaction of Aldehydes and Ketones with Dichloroisopropoxyborane. Comparison of the Reducing Characteristics of Isopropoxyborane Derivatives / 29 (4) , 885
11	(2007) Bulletin of the Korean Chemical Society Regioselective Ring Cleavage of Phenyl- or/and Alkyl- Substituted Epoxides with Al-Methanesulfonyldiisobutylalane / 30 (11) , 2823
4	Jin-Soon Cha. (2007) Bulletin of the Korean Chemical Society Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane / 31 (4) , 840
8	Jin-Soon Cha. (2007) Bulletin of the Korean Chemical Society Regioselective Ring Cleavage of Phenyl- or/and Alkyl-Substituted Epoxides with Al-Trifluoromethanesulfonyldiisobutylalane. Comparison of Its Reactivity with Al-Methanesulfonyldiisobutylalane / 31 (8) , 2135
1	Jin-Soon Cha. (2011) Bulletin of the Korean Chemical Society Selective Reduction of Organic Compounds with Al-Trifluoromethanesulfonyldiisobutylalane. Comparison of Its Reactivity with Al-Methanesulfonyldiisobutylalane / 32 (1) , 219
22	M. Carmen de la Fuente. (2007) Tetrahedron Normal electron demand Diels–Alder cycloaddition of indoles to 2,3-dimethyl-1,3-butadiene / 67 (22) , 3997
7	Kyle Flack. (2007) Organic process research & development Al(OtBu)<SUB>3</SUB> as an Effective Catalyst for the Enhancement of Meerwein–Ponndorf–Verley (MPV) Reductions / 16 (7) , 1301
2	Keepyung Nahm. (2007) Bulletin of the Korean Chemical Society MPV-Reduction of C=O bond with Al-substituted-dialkylalan; A Theoretical Study on Relative Reactivity of Various Carbonyl Substrates / 35 (2) , 546
9	(2020) Energy & fuels : an American Chemical Society journal Thermal Reduction of CO<SUB>2</SUB> with Activated Alkali Metal Aluminum Hydrides for Selective Methanation / 34 (9) , 11210
7	Yong-Qing Yang. (2007) Chinese journal of chemistry A Convenient Heterogeneous Reduction of Knoevenagel Product by Hantzsch Ester and Its Development into Reductive Alkylation of Malononitrile / 32 (7) , 650
None	Thomas Pasini. (2014) Journal of catalysis Methanol as a clean and efficient H-transfer reactant for carbonyl reduction: Scope, limitations, and reaction mechanism / 317 (None) , 206

1	/ Journal of Inclusion Phenomena
2	/ Journal of Inclusion Phenomena
3	/ Bulletin of the Korean Chemical Society