Asymmetric synthesis of (αS)-polyfluoroalkylated N-Boc-prolinols by the diethyl zinc-induced asymmetric Meerwein–Ponndorf–Verley reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones

Literature Information

Publication Date 2015-02-11
DOI 10.1039/C5QO00008D
Impact Factor 5.281
Authors

Kazumasa Funabiki, Hiroki Iwata, Yosuke Yano, Yasuhiro Kubota, Masaki Matsui


View Original

Abstract

The reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones with diethyl zinc was investigated. As a result, asymmetric Meerwein–Ponndorf–Verley reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones proceeded smoothly with the use of 5 equiv. of diethyl zinc as a reducing agent in hexane at room temperature to give (αS)-polyfluoroalkylated N-Boc-prolinols in good yields (31–73%) with high diastereomer ratios (up to αR/αS = 7/93). The absolute configuration at the α-position of the major diastereomer is opposite to that obtained by the reduction of N-Boc-pyrrolidyl ketone with NaBH4 in ethanol. Furthermore, we also achieved the tandem perfluorobutylation-MPV reduction of N-Boc-proline ethyl ester to give (αS)-perfluorobutylated N-Boc-prolinol as a sole diastereomer in 45% yield.

Related Literature

On the role of gold nanoparticles in the selective photooxidation of 2-propanol over Au/TiO2

Alexander Lüken, Martin Muhler, Jennifer Strunk

2015-03-13 Paper

DOI: 10.1039/C4CP05423G

Fragmentation mechanisms of cytosine, adenine and guanine ionized bases

Leila Sadr-Arani, Pierre Mignon, Henry Chermette, Hassan Abdoul-Carime, Bernadette Farizon, Michel Farizon

2015-03-31 Paper

DOI: 10.1039/C5CP00104H

Large electric-field-induced strain in centrosymmetric crystals of a dipolar ruthenium alkynyl complex

K. Lau, A. Barlow, G. J. Moxey, Q. Li, Y. Liu, M. G. Humphrey, M. P. Cifuentes, T. J. Frankcombe, R. Stranger

2015-03-18 Paper

DOI: 10.1039/C5CP00528K

Elucidating factors important for monovalent cation selectivity in enzymes: E. coli β-galactosidase as a model

Robert W. Wheatley, Douglas H. Juers, Bogdan B. Lev, Reuben E. Huber, Sergei Yu. Noskov

2015-03-20 Paper

DOI: 10.1039/C4CP04952G

Enhancing electrochemical performance by control of transport properties in buffer layers – solid oxide fuel/electrolyser cells

Devaraj Ramasamy, Narendar Nasani, Ana D. Brandão, Domingo Pérez Coll, Duncan P. Fagg

2015-04-02 Paper

DOI: 10.1039/C5CP00778J

Towards a comprehensive insight into efficient hydrogen production by self-assembled Ru(bpy)32+–polymer–Pt artificial photosystems

Huan Lin, Dan Liu, Jinlin Long, Zizhong Zhang, Huaqiang Zhuang, Yi Zheng, Xuxu Wang

2015-03-13 Paper

DOI: 10.1039/C5CP00720H

Adsorptive desulfurization with CPO-27/MOF-74: an experimental and computational investigation

Ben Van de Voorde, Markéta Hezinová, Jeroen Lannoeye, Annelies Vandekerkhove, Bartosz Marszalek, Barbara Gil, Isabelle Beurroies, Petr Nachtigall, Dirk De Vos

2015-03-20 Paper

DOI: 10.1039/C5CP01063B

XPS of guanidinium ionic liquids: a comparison of charge distribution in nitrogenous cations

Ana R. Santos, Rebecca K. Blundell, Peter Licence

2015-04-02 Paper

DOI: 10.1039/C5CP01069A

Rydberg and valence state excitation dynamics: a velocity map imaging study involving the E–V state interaction in HBr

Dimitris Zaouris, Andreas Kartakoullis, Pavle Glodic, Peter C. Samartzis, Helgi Rafn Hróðmarsson, Ágúst Kvaran

2015-03-16 Paper

DOI: 10.1039/C5CP00748H

You might also like

Compound Q&A

Is 2-(2-chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) safe?

2-(2-Chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) is generally consi...

7765-11-92-(2-chloroacetamido...
Compound Q&A

Is 2-(Benzyloxy)-5-bromobenzoic acid (CAS: 62176-31-2) safe?

2-(Benzyloxy)-5-bromobenzoic acid can be handled safely if appropriate precautio...

62176-31-22-(Benzyloxy)-5-brom...
Compound Q&A

What is (4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride (CAS: 1159825-48-5)?

(4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride is a chemical compound ...

1159825-48-5(4-Methyl-1,2,5-oxad...
Compound Q&A

What is 2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54-7)?

2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54...

917985-54-72-(5-Hexylthiophen-2...
Compound Q&A

Are there alternatives to 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS: 102771-26-6) in synthesis?

While 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS:...

102771-26-64-(8-Methyl-9H-1,3-d...
Compound Q&A

What is the market or research trend for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine-6-carboxylate (CAS: 851376-80-2)?

The market for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine...

851376-80-2tert-butyl 3-hydroxy...
Compound Q&A

How should waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) be handled?

Waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) should ...

6844-58-23,5-Diamino-1H-pyraz...
Compound Q&A

How is (6-Fluoro-3-pyridinyl)boronic acid (CAS: 351019-18-6) typically synthesized?

(6-Fluoro-3-pyridinyl)boronic acid can be synthesized through the reaction of 6-...

351019-18-6(6-Fluoro-3-pyridiny...
Compound Q&A

What industries use Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9)?

Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9) finds applications in vario...

10065-79-9Dibenzyl carbonimido...
Compound Q&A

What is the market or research trend for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4)?

The market for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4) is g...

74228-83-4(beta,beta,2,3,4,5,6...

Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.