132065-12-4Relevant articles and documents
New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
Barrett, Stephen,O'Brien, Peter,Steffens, H.Christian,Towers, Timothy D,Voith, Matthias
, p. 9633 - 9640 (2007/10/03)
A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are presented. (C) 2000 Elsevier Science Ltd.
Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
O'Brien, Peter,Towers, Timothy D.,Voith, Matthias
, p. 8175 - 8178 (2007/10/03)
Several N-mono- and diprotected alkenes have been prepared and the stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base-mediated rearrangement of a cis-monoprotected epoxide generated the corresponding amino-cyclopentenol in good yield and with an enantiomeric excess of 60%.
HYDROGEN BOND DIRECTED NITRILE OXIDE CYCLOADDITION REACTIONS OF ALLYLIC 2o-AMIDES
Curran, Dennis P.,Gothe, Scott A.,Choi, Sung-Mo
, p. 1371 - 1395 (2007/10/02)
The ability of allylic and homoallylic 2o-amides to direct nitrile oxide cycloaddition reactions has been studied.For N-cyclopentenyl amides, good regio- and stereochemical control are observed and mechanistic studies suggest that hydrogen bond
(+/-)-Carbocyclic 5'-Nor-2'-deoxyguanosine and Related Purine Derivatives: Synthesis and Antiviral Properties
Patil, Sharadbala D.,Koga, Masakazu,Schneller, Stewart W.,Snoeck, Robert,Clercq, Erik De
, p. 2191 - 2195 (2007/10/02)
Beginning with 3-cyclopenten-1-ylamine hydrochloride, the 5'-nor derivatives of carbocyclic 2'-deoxyguanosine (2), 2'-deoxyadenosine (3),, and 2,6-diaminopurine 2'-deoxyribofuranoside (4) have been prepared.These compounds were evaluated for antiviral pot
The synthesis of two 2'-deoxy carbocyclic purine nucleosides lacking the 5'-methylene
Koga,Schneller
, p. 5861 - 5864 (2007/10/02)
The synthesis of the adenine derivative (±)-(1α,2β,4α)-4-(6-amino-9H-purin-9-yl)-1,2-cyclopentanediol (2) and its hypoxanthine analogue (3) as carbocyclic nucleosides lacking the 5'-methylene is described in 7 steps from 3-cyclopenten-1-ylamine hydrochlor