One-Pot and Stereospecific Synthesis of cis-1,2-Diazides via Mitsunobu Reaction of Epoxides.

ChemInform ◽  
2003 ◽  
Vol 34 (10) ◽  
Author(s):  
Sueleyman Goeksu ◽  
Hasan Secen ◽  
Yasar Suetbeyaz
Keyword(s):  
Mitsunobu Reaction ◽  
Stereospecific Synthesis ◽  
One Pot

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4215-4230 ◽  
Author(s):  
Adesh Kumar Singh ◽  
Rapelly Venkatesh ◽  
Jeyakumar Kandasamy
Keyword(s):  
Room Temperature ◽  
Stereospecific Synthesis ◽  
One Pot ◽  
Tert Butyl ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
Aryl Glycosides

The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

One-pot kinetic resolution–Mitsunobu reaction to access optically pure compounds, using silver salts in the substitution protocol

2020 ◽  
Vol 44 (48) ◽  
pp. 21238-21243
Author(s):  
Hiten B. Raval ◽  
Ashutosh V. Bedekar
Keyword(s):  
Kinetic Resolution ◽  
Mitsunobu Reaction ◽  
One Pot ◽  
Silver Salts ◽  
Pure Compounds ◽  
Optically Pure

Racemic carbinols were converted to chirally pure acetates by a combination of one-pot, enzyme mediated KR and Mitsunobu reaction with metal acetates. Use of AoNO3 or mixture with NaOAc gave excellent results. The protocol is further extended to introduce azide in place of acetate.

Stereospecific Synthesis of (-)-allo-Muscarine from D-Glucose: Novel Routes to the Key Chiral Synthon

1997 ◽  
Vol 62 (5) ◽  
pp. 809-815 ◽  
Author(s):  
Velimir Popsavin ◽  
Ostoja Beric ◽  
Mirjana Popsavin ◽  
János Csanádi ◽  
Stevan Lajšic ◽  
...  
Keyword(s):  
Mitsunobu Reaction ◽  
Stereospecific Synthesis ◽  
Novel Synthesis ◽  
Derivatives Of ◽  
Chiral Synthon ◽  
Ethylene Acetal

The key chiral synthon in a novel synthesis of (-)-allo-muscarine from D-glucose has been prepared by three independent routes. The most efficient one includes a four-step conversion via the 4-O-benzoyl derivatives of starting 2,5-anhydro-3,5-di-O-methanesulfonyl-L-idose ethylene acetal (2a) into 2,5-anhydro-3,6-dideoxy-L-lyxo-hexose ethylene acetal (4b). The intermediate 4b was efficiently converted into the chiral synthon 2,5-anhydro-4-O-benzoyl-3,6-dideoxy-L-arabino-hexose (4c) by Mitsunobu reaction.

scholarly journals Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

2016 ◽  
Vol 12 ◽  
pp. 662-669 ◽  
Author(s):  
Guozheng Huang ◽  
Simon Schramm ◽  
Jörg Heilmann ◽  
David Biedermann ◽  
Vladimír Křen ◽  
...  
Keyword(s):  
Mitsunobu Reaction ◽  
Synthetic Method ◽  
One Pot ◽  
Selective Esterification ◽  
C 23 ◽  
High Yields

Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biologically important enantiomers of hydnocarpin D, hydnocarpin and isohydnocarpin, respectively. This represents the only one-pot semi-synthetic method to access these flavonolignans in high yields.

One-Pot and Stereospecific Synthesis ofcis-1,2-Diazides via Mitsunobu Reaction­ of Epoxides

Synthesis ◽  
2002 ◽  
pp. 2373-2378 ◽  
Author(s):  
Hasan Seçen ◽  
Yasar Sütbeyaz ◽  
Süleyman Göksu
Keyword(s):  
Stereospecific Synthesis ◽  
One Pot

scholarly journals Direct Stereospecific Synthesis of Unprotected N-H and N-Me Aziridines from Olefins

Science ◽  
2014 ◽  
Vol 343 (6166) ◽  
pp. 61-65 ◽  
Author(s):  
Jawahar L. Jat ◽  
Mahesh P. Paudyal ◽  
Hongyin Gao ◽  
Qing-Long Xu ◽  
Muhammed Yousufuddin ◽  
...  
Keyword(s):  
Natural Products ◽  
Ambient Temperature ◽  
Building Block ◽  
Direct Synthesis ◽  
Stereospecific Synthesis ◽  
Quantum Mechanical ◽  
Quantum Mechanical Calculations ◽  
One Pot ◽  
Rhodium Catalysis ◽  
Bioactive Natural Products

Despite the prevalence of the N-H aziridine motif in bioactive natural products and the clear advantages of this unprotected parent structure over N-protected derivatives as a synthetic building block, no practical methods have emerged for direct synthesis of this compound class from unfunctionalized olefins. Here, we present a mild, versatile method for the direct stereospecific conversion of structurally diverse mono-, di-, tri-, and tetrasubstituted olefins to N-H aziridines usingO-(2,4-dinitrophenyl)hydroxylamine (DPH) via homogeneous rhodium catalysis with no external oxidants. This method is operationally simple (i.e., one-pot), scalable, and fast at ambient temperature, furnishing N-H aziridines in good-to-excellent yields. Likewise, N-alkyl aziridines are prepared from N-alkylated DPH derivatives. Quantum-mechanical calculations suggest a plausible Rh-nitrene pathway.

Stereospecific Synthesis of (+)-Muscarine from D-Glucose, Suitable for Preparation of 5-Substituted Analogues

1998 ◽  
Vol 63 (10) ◽  
pp. 1522-1527 ◽  
Author(s):  
Velimir Popsavin ◽  
Ostoja Beric ◽  
Ljubica Radic ◽  
Mirjana Popsavin ◽  
Vera Cirin-Novta ◽  
...  
Keyword(s):  
Catalytic Hydrogenation ◽  
Mitsunobu Reaction ◽  
Stereospecific Synthesis ◽  
Key Steps ◽  
Stereospecific Cyclization

A stereospecific synthesis of (+)-muscarine iodide (1) has been achieved starting from D-glucose as a chiral precursor. The key steps of the synthesis involved a stereospecific cyclization of 3,5-di-O-mesyl derivative 3 into the 2,5-anhydride 4, the stereospecific catalytic hydrogenation of unsaturated derivative 6, and the C-4 epimerization of alcohol 12 by Mitsunobu reaction.

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