939-21-9Relevant articles and documents
Acceleration of a dipolar Claisen rearrangement by hydrogen bonding to a soluble diaryl urea
Curran, Dennis P.
, p. 6647 - 6650 (1995)
The Claisen rearrangement of 6-methoxy allyl vinyl ether is catalyzed by a soluble diaryl urea, and evidence is presented that the urea stabilizes a dipolar transition state by hydrogen bonding.
Enantioselective Iridium-Catalyzed α-Allylation with Aqueous Solutions of Acetaldehyde
Carreira, Erick M.,Sandmeier, Tobias
supporting information, (2020/02/15)
The enantioselective α-allylation of aqueous solutions of acetaldehyde using iridium- A nd amine-catalyzed substitution of racemic allylic alcohols is described. The method utilizes a readily available, safely handled aqueous solution of acetaldehyde and furnishes ?,?-unsaturated aldehydes in good yields and greater than 99% enantiomeric excess. The synthetic potential of the method is demonstrated with the enantioselective formal syntheses of heliannuols C and E as well as heliespirones A and C.
Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst
Uyeda, Christopher,Jacobsen, Eric N.
supporting information; scheme or table, p. 9228 - 9229 (2009/02/03)
N,N-Diphenylguanidinium ion associated with the noncoordinating BArF counterion is shown to be an effective catalyst for the [3,3]-sigmatropic rearrangement of a variety of substituted allyl vinyl ethers. Highly enantioselective catalytic Claisen rearrangements of ester-substituted allyl vinyl ethers are then documented using a new C2-symmetric guanidinium ion derivative. Copyright
One-pot Claisen rearrangement with n-butyl vinyl ether
Tokuyama, Hidetoshi,Makido, Takaki,Ueda, Toshihiro,Fukuyama, Tohru
, p. 869 - 873 (2007/10/03)
A protocol for one-pot Claisen rearrangement with n-butyl vinyl ether is described. Upon heating allylic alcohols with excess n-butyl vinyl ether with catalytic amount of Hg(OAc)2 and NaOAc, Claisen rearrangement takes place through in situ formation of the requisite allyl vinyl ether.