scholarly journals Asymmetric synthesis of 1,2-fluorohydrin: iridium catalyzed hydrogenation of fluorinated allylic alcohol

2020 ◽  
Vol 11 (41) ◽  
pp. 11189-11194
Author(s):  
Sudipta Ponra ◽  
Jianping Yang ◽  
Haibo Wu ◽  
Wangchuk Rabten ◽  
Pher G. Andersson
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation ◽  
Allylic Alcohol ◽  
Allylic Alcohols ◽  
Iridium Complex ◽  
Simple Protocol

We have developed a simple protocol for the preparation of 1,2-fluorohydrin by asymmetric hydrogenation of fluorinated allylic alcohols using an efficient azabicyclo thiazole-phosphine iridium complex.

scholarly journals Asymmetric Hydrogenation of Allylic Alcohols Using Ir–N,P-Complexes

ACS Catalysis ◽  
2016 ◽  
Vol 6 (12) ◽  
pp. 8342-8349 ◽  
Author(s):  
Jia-Qi Li ◽  
Jianguo Liu ◽  
Suppachai Krajangsri ◽  
Napasawan Chumnanvej ◽  
Thishana Singh ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Allylic Alcohols

Cyanoalkylation/alkynylation of allylic alcohol through intramolecular radical 1,2-alkynyl migration

2021 ◽  
Vol 19 (11) ◽  
pp. 2416-2419
Author(s):  
Shengnan Jin ◽  
Fan Chen ◽  
Pengcheng Qian ◽  
Jiang Cheng
Keyword(s):  
Allylic Alcohol ◽  
Allylic Alcohols ◽  
Butyl Peroxide

A di-tert-butyl peroxide (DTBP)-promoted difunctionalization of α-aryl α-alkynyl allylic alcohols with alkyl nitriles was developed, affording a series of α-alkynyl γ-cyano functionalized ketones in moderate yields.

Functional Group Transformation: The Castle Synthesis of Celogentin C

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Allylic Alcohol ◽  
Efficient Reduction ◽  
Simple Protocol ◽  
Peking University ◽  
Celogentin C ◽  
Purdue University ◽  
Institute Of Technology ◽  
Tertiary Amides ◽  
The University ◽  
Functional Group Transformation

Mark Cushman of Purdue University found (J. Org. Chem. 2010, 75, 3507) that a benzylic methyl ether 1 could be converted to the aldehyde 2 by N -bromosuccinimide. Two equivalents of NBS gave the methyl ester. Ning Jiao of Peking University used (Organic Lett. 2010, 12, 2888) NaN3 followed by DDQ to oxidize a benzylic halide 3 to the nitrile 4. Hugues Miel of Almac Sciences oxidized (Tetrahedron Lett. 2010, 51, 3216) the ketone 5 to the nitro derivative 6. The oxidative conversion of the nitro compound 7 to the ketone 8 described (Tetrahedron Lett. 2009, 50, 6389) by Vera L. Patrocinio Pereira of the Universidade Federal do Rio de Janeiro proceeded without epimerization. Sundarababu Baskaran of the Indian Institute of Technology Madras established (Angew. Chem. Int. Ed. 2010, 49, 804) that oxidative cleavage of the benzylidene acetal 9 delivered 10 with high regioselectivity. The intramolecular alkene dihydroxylation of 11 originated (Angew. Chem. Int. Ed. 2010, 49, 4491) by Erik J. Alexanian of the University of North Carolina gave 12 with high diastereocontrol. Ruimao Hua of Tsinghua University took advantage (J. Org. Chem. 2010, 75, 2966) of the H-donor properties of DMF to develop an efficient reduction of the alkyne 13 to the alkyne 14 . Alejandro F. Barrero of the University of Granada developed (J. Am. Chem. Soc. 2010, 132, 254) Ti (III) conditions for the reduction of the allylic alcohol 15 to the terminal alkene 16. Isolated alkenes were stable to these conditions. P. Veeraraghavan Ramachandran, also of Purdue University, effected (Tetrahedron Lett. 2010, 51, 3167) reductive amination of 17 to 18 using the now readily available NH3 - BH3 . Bin Ma and Wen-Cherng Lee of BiogenIdec developed (Tetrahedron Lett. 2010, 51, 385) a simple protocol for the conversion of an acid 19 to the free amine 20. Marc Lemaire of Université Lyons 1 established (Tetrahedron Lett. 2010, 51, 2092) that the silane 22 reduced primary, secondary, and tertiary amides to the aldehydes.

ChemInform Abstract: The Asymmetric Synthesis of Allylic Alcohols Using a Recoverable Chiral Sulfoxide.

ChemInform ◽  
2010 ◽  
Vol 25 (34) ◽  
pp. no-no
Author(s):  
I. D. LINNEY ◽  
H. TYE ◽  
M. WILLS ◽  
R. J. BUTLIN
Keyword(s):  
Asymmetric Synthesis ◽  
Allylic Alcohols

Asymmetric Synthesis of Monoprotected Double Allylic Alcohols

Synthesis ◽  
2002 ◽  
pp. 1571-1577 ◽  
Author(s):  
Dieter Enders ◽  
Matthias Voith
Keyword(s):  
Asymmetric Synthesis ◽  
Allylic Alcohols
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