3230-69-1Relevant articles and documents
Diastereoselectivity in the Carroll rearrangement of β-keto esters of tertiary allylic alcohols
Jung, Michael E.,Duclos, Brian A.
, p. 107 - 109 (2004)
Carroll rearrangement of β-keto esters derived from tertiary allylic alcohols, for example, 7, under basic conditions followed by decarboxylation of the resulting β-keto acids yielded the expected γ, δ-unsaturated methyl ketones 8 with a range of olefin geometries from 100:0 to 1:1.8 E/Z, depending on the relative steric requirements of the two groups at the allylic center.
Evidence for concerted processes in the course of the homoallenylic transposition
Aouf, Chahinez,Galy, Nicolas,Santelli, Maurice
supporting information, p. 3225 - 3233 (2013/04/24)
The hydrolysis of β-allenic tosylates produces mainly 2-methylenecyclobutanols resulting from a homoallenylic participation along with isomeric 2-methylenecyclobutanol minor products coming from a 1234-1243 rearrangement. Structures of various cyclopropylvinyl carbocations involved in the course of the hydrolysis have been determined by computational studies. For acyclic tosylates, the hydrolysis of one β-deuterated allenic tosylate confirmed the nucleophilic attack on the corresponding nonclassical carbonium ion before its evolution to a more stable cyclopropylvinyl carbocation. In the case of one cyclic β-allenic tosylate, the structure of the products has been checked by the use of deuterated isotopomer.
A general and facile synthesis of substituted furans by palladium- catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols
Gabriele,Salerno,Lauria
, p. 7687 - 7692 (2007/10/03)
A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 °C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.
