Cu(I)-Catalyzed Coupling of (9-Benzylpurin-6-yl)magnesium Chloride with Allyl Halides: An Approach to 6-Allylpurine Derivatives

2006 ◽  
Vol 71 (8) ◽  
pp. 1221-1228 ◽  
Author(s):  
Martin Klečka ◽  
Tomáš Tobrman ◽  
Dalimil Dvořák
Keyword(s):  
Double Bond ◽  
Magnesium Chloride ◽  
Allylic Rearrangement ◽  
Allyl Halides ◽  
Purine Ring

6-Allylpurine derivatives are formed by Cu(I)-catalyzed coupling of (9-benzyl-9H-purin-6-yl)- magnesium chloride with allyl halides. The reaction is accompanied by allylic rearrangement in some cases. Under acid conditions the double bond of the allyl group rearranges to the conjugation with purine ring.

Evidence for a cytochrome P-450-catalyzed allylic rearrangement with double-bond topomerization

1988 ◽  
Vol 110 (6) ◽  
pp. 1979-1981 ◽  
Author(s):  
Robert H. McClanahan ◽  
Alain C. Huitric ◽  
Paul G. Pearson ◽  
John C. Desper ◽  
Sidney D. Nelson
Keyword(s):  
Double Bond ◽  
Allylic Rearrangement ◽  
Cytochrome P 450

An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1437-1441
Author(s):  
Xu yan Cao ◽  
Fei Huang ◽  
Songlin Zhang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Type Reaction ◽  
Mild Conditions ◽  
Allyl Halides ◽  
Barbier Reaction

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3446-3451
Author(s):  
Songlin Zhang ◽  
Dengbing Xie ◽  
Yiqiong Wang ◽  
Bo Yang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
Carbon Double Bond ◽  
Allyl Halides ◽  
First Time

The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

Microbial hydroxylation of steroids. 10. Rearrangement during epoxidation and hydroxylation, and the stepwise nature of these enzymic reactions

1985 ◽  
Vol 63 (5) ◽  
pp. 1121-1126 ◽  
Author(s):  
Herbert L. Holland ◽  
Elly Riemland
Keyword(s):  
Double Bond ◽  
Product Formation ◽  
Enzymatic Oxidation ◽  
Allylic Rearrangement ◽  
Stepwise Mechanism ◽  
Microbial Hydroxylation ◽  
A Site

A series of unsaturated steroids has been incubated with fungi which are known to hydroxylate at a site corresponding to the allylic position in the analogous saturated steroids. In some cases, the anticipated hydroxylation occurred without rearrangement of the double bond. In a number of instances, however, products were obtained whose structures implied that allylic rearrangement had occurred during the reaction. The formation of these products is consistent with a stepwise mechanism of enzymatic oxidation. Possible routes for product formation are presented which incorporate this proposal.

Reevaluation of the stereochemical courses of the allylic rearrangement and the double-bond reduction catalyzed by Brevibacterium ammoniagenes fatty acid synthase

1991 ◽  
Vol 113 (10) ◽  
pp. 3997-3998 ◽  
Author(s):  
Mary C. O'Sullivan ◽  
John M. Schwab ◽  
T. Mark Zabriskie ◽  
Gregory L. Helms ◽  
John C. Vederas
Keyword(s):  
Fatty Acid ◽  
Double Bond ◽  
Fatty Acid Synthase ◽  
Allylic Rearrangement
Sign in / Sign up

Export Citation Format

Share Document