On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule

Tetrahedron ◽  
1984 ◽  
Vol 40 (12) ◽  
pp. 2247-2255 ◽  
Author(s):  
J.K. Cha ◽  
W.J. Christ ◽  
Y. Kishi
Keyword(s):  
Allylic Alcohol ◽  
Osmium Tetraoxide ◽  
Empirical Rule

Synthesis of the C19–C30 Bis-THF Fragment of Iriomoteolide-13a via Stepwise SN2 Cyclization and Intramolecular syn-Oxypalladation

2020 ◽  
Author(s):  
Hui Zhao ◽  
Kai Gao ◽  
Haichen Ma ◽  
Tsz Chun Yip ◽  
Wei-Min Dai
Keyword(s):  
Aldol Reaction ◽  
Allylic Alcohol ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Groups

The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The w-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by <i>anti</i>-aldol reaction and asymmetric dihydroxylation (AD). Upon heating in pyridine the stereotetrad underwent an S<sub>N</sub>2 cyclization to form the C19–C22 THF ring. It was followed by an intramolecular <i>syn</i>-oxypalladation of the C28 chiral allylic alcohol to give the C23–C26 THF ring.

scholarly journals Synthesis of a sucrose dimer with enone tether; a study on its functionalization

2014 ◽  
Vol 10 ◽  
pp. 1246-1254 ◽  
Author(s):  
Zbigniew Pakulski ◽  
Norbert Gajda ◽  
Magdalena Jawiczuk ◽  
Jadwiga Frelek ◽  
Piotr Cmoch ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Double Bond ◽  
Carbonyl Group ◽  
Osmium Tetroxide ◽  
Cd Spectroscopy ◽  
Allylic Alcohol ◽  
Circular Dichroïsm

The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology.

Synthesis of allylic alcohol single-chain PGH analogs. A synthetic application of the argon laser

1986 ◽  
Vol 51 (21) ◽  
pp. 4028-4035 ◽  
Author(s):  
R. Marshall Wilson ◽  
Karlyn A. Schnapp ◽  
Richard K. Merwin ◽  
Revathi Ranganthan ◽  
David L. Moats ◽  
...  
Keyword(s):  
Argon Laser ◽  
Allylic Alcohol ◽  
Single Chain ◽  
Synthetic Application

scholarly journals Allylic Alcohol Synthesis by Ni-Catalyzed Direct and Selective Coupling of Alkynes and Methanol

2021 ◽  
Author(s):  
Herong chen ◽  
Zhijun Zhou ◽  
Wangqing Kong
Keyword(s):  
Coupling Reaction ◽  
Allylic Alcohol ◽  
Raw Material ◽  
Alcohol Synthesis

Methanol is an abundant and renewable chemical raw material, but its use as a C1 source in C-C bond coupling reaction still constitutes a big challenge, and the known methods...

Carboncarbon bond formation by reactions of allylic alcohol with enoxysilane in the presence of Ir-complex

2002 ◽  
Vol 43 (6) ◽  
pp. 1043-1046 ◽  
Author(s):  
Isamu Matsuda ◽  
Shogo Wakamatsu ◽  
Ken-ichi Komori ◽  
Tatsuya Makino ◽  
Kenji Itoh
Keyword(s):  
Bond Formation ◽  
Allylic Alcohol ◽  
Carbon Bond ◽  
Carbon Carbon Bond
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