159910-03-9Relevant articles and documents
Second generation levoglucosenone-derived chiral auxiliaries. Scope and application in asymmetric Diels-Alder reactions
Sarotti, Ariel M.,Spanevello, Rolando A.,Suárez, Alejandra G.
supporting information; experimental part, p. 3502 - 3508 (2009/08/15)
Chiral alcohols were designed and easily prepared from levoglucosenone, a biomass-derived valuable synthon. These alcohols were tested as chiral auxiliaries in asymmetric Diels-Alder reactions between the corresponding acrylates with acyclic and cyclic di
Synthesis of fused cyclic systems containing medium-sized rings through tandem ROM-RCM of norbornene derivatives embedded in a carbohydrate template
Malik, Chanchal K.,Yadav, Ram Naresh,Drew, Michael G. B.,Ghosh, Subrata
supporting information; experimental part, p. 1957 - 1963 (2009/08/07)
A general approach for the synthesis of fused cyclic systems containing medium-sized rings (7-9) has been developed. The key steps involve a diastereoface-selective Diels-Alder reaction of the dienophiles 4a-d attached to a furanosugar with cyclopentadiene and ring opening (ROM)-ring closing metathesis (RCM) of the resulting norbornene derivatives 10a-d and 11a-d. Diels-Alder reaction of the dienophiles 4a-d with cyclopentadiene in the absence of a catalyst produced 10a-d as the major product arising through addition of the diene to the unhindered Si-face. The most interesting and new aspect of the Diels-Alder reaction of these dienophiles is the accessibility of the Re-face that was blocked by the alkenyl chains under Lewis acid catalysis producing the diastereoisomers 11a-d exclusively. The reversal of facial selectivity from an uncatalyzed reaction to a catalyzed one is unprecedented. The observed stereochemical dichotomy is attributed to rotation of the enone moiety along the o bond linking the sugar moiety during formation of the chelate 13. This makes the Re-face of the enone moiety in 4a-d unhindered. Diels-Alder reaction of the carbocyelic analogue 15 under Lewis acid catalysis produced a 1:1 mixture of the adducts 16 and 17 confirming the participation of sugar ring oxygen in chelate formation. Finally ROM-RCM of 10a-d and 11a-d with Grubbs' catalyst afforded the cis-syn-cis and cis-anti-cis bicyclo-annulated sugars 21a-d and 23a-d, respectively, containing 7-9 membered rings.
(R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels-Alder reactions
Akkari, Rhalid,Calmes, Monique,Escale, Francoise,Iapichella, Julien,Rolland, Marc,Martinez, Jean
, p. 2515 - 2525 (2007/10/03)
The synthesis of enantiopure (R)- and (S)-4-(3-hydroxy-4,4-dimethyl-2- oxopyrrolidin-1-yl)benzoic acid is described and the corresponding supported chiral acrylate derivative has been used as a dienophile in solid phase asymmetric Diels-Alder reactions wi
2,5-diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions
Le, Thuy X.H.,Bussolari, Jacqueline C.,Murray, William V.
, p. 3849 - 3852 (2007/10/03)
Diketopiperazines have been utilized as chiral auxiliaries for asymmetric Diels-Alder reactions. Cyclo-S-phenylalanyl-R-proline (2) was found to be the most promising of these auxiliaries and afforded Diels-Alder adducts in high chemical yield (78-95%), with endo selectivities generally greater than 9:1. The diastereoselectivities observed were comparable to the best previously published values.
Dispiroketals in Synthesis (Part 13): Functionalised Dispiroketals as New Chiral Auxiliaries; Highly Stereoselective Diels-Alder Reactions using a Bifunctional, C2-Symmetrical Chiral Auxiliary.
Bezuidenhoudt, Barend C. B.,Castle, Grant H.,Geden, Joanna V.,Ley, Steven V.
, p. 7451 - 7454 (2007/10/02)
Highly selective, asymmetric, Lewis acid catalysed Diels-Alder reactions are reported with a bifunctional, C2-symmetrical diacrylate derivative obtained from a chiral auxiliary based on dihydroxylated dispiroketals.
Methyl 3,4-O-methylene-β-D-arabinoside as a new Chiral Template for the Asymmetric Diels-Alder Reaction
Nouguier, Robert,Gras, Jean-Louis,Giraud, Bouchra,Virgili, Albert
, p. 5529 - 5530 (2007/10/02)
The acrylate of the methyl 3,4-O-methylene-β-D-arabinoside is a very stable and efficient chiral dienophile for asymmetric Diels-Alder reactions with cyclopentadiene, isoprene and dimethyl butadiene.Key words: Asymmetric Diels-Alder reaction, carbohydrate