69248-81-3Relevant articles and documents
STEREOCHEMISTRY OF THE Pd(PPh3)4-CATALYZED CONVERSION OF 1-BROMOALLENES INTO PHENYL SUBSTITUTED ALLENES.
Elsevier, C.J.,Mooiweer, H.H.,Kleijn, H.,Vermeer, P.
, p. 5571 - 5572 (1984)
1-Bromoallenes 1 are converted into the phenyl substituted allenes 2 with inversion of configuration in the allenyl moiety by reaction with Ph2Zn using Pd(PPh3)4 as catalyst.
A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes
Arai, Shigeru,Hori, Hiroto,Amako, Yuka,Nishida, Atsushi
supporting information, p. 7493 - 7496 (2015/05/04)
Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is
Stereoretentive suzuki-miyaura coupling of haloallenes enables fully stereocontrolled access to (-)-Peridinin
Woerly, Eric M.,Cherney, Alan H.,Davis, Erin K.,Burke, Martin D.
supporting information; experimental part, p. 6941 - 6943 (2010/08/06)
Stimulated by the substantial challenge of synthesizing the complex and sensitive stereogenic allene-containing core of (-)-peridinin, the first stereocontrolled coupling of haloallenes with boronic acids has been achieved. This new method and the principles that emerged during its development stand to enable the more efficient and flexible preparation of a wide range of natural products, pharmaceuticals, and intermediates that possess a stereogenic allene motif. This new reaction was harnessed to achieve the first completely stereocontrolled total synthesis of (-)-peridinin. This synthesis was accomplished using only one reaction iteratively to assemble four fully functionalized building blocks with complete stereoretention at each initial halide or boron-bearing carbon. This synthesis elevates the capacity of the iterative cross-coupling strategy to an unprecedented benchmark. Moreover, the efficient and highly modular nature of this synthesis promises to enable systematic dissection of the heretofore enigmatic structure/function relationships that underlie the protein-like antilipoperoxidant activities of this remarkable small molecule natural product.