905309-65-1Relevant academic research and scientific papers
Enantioselective allylation and crotylation of in situ generated β,γ-unsaturated aldehydes
McCubbin, J. Adam,Maddess, Matthew L.,Lautens, Mark
supporting information; experimental part, p. 2857 - 2861 (2012/01/11)
β,γ-Unsaturated aldehydes generated in situ by treatment of 2-vinyloxiranes with a catalytic amount of Sc(OTf)3 are effectively trapped by ring-strained allyl- and crotylsilane reagents to afford bishomoallylic alcohols as single diastereomers in high enantiomeric excess. Georg Thieme Verlag Stuttgart · New York.
Total synthesis of cryptophycin analogues via a scaffold approach
McCubbin, J. Adam,Maddess, Matthew L.,Lautens, Mark
, p. 2993 - 2996 (2007/10/03)
Allylation of in situ generated β,γ-unsaturated aldehydes affords rapid access to vinyl halide analogues of fragment A of the cryptophycins. Three scaffolds are prepared in gram quantities by a ring-closing metathesis approach. Derivatization via a variety of cross-coupling protocols is possible, which affords novel analogues of these potent antimitotic agents.
Enantioselective allylation of β,γ-unsaturated aldehydes generated via Lewis acid induced rearrangement of 2-vinyloxiranes
Lautens, Mark,Maddess, Matthew L.,Sauer, Effiette L. O.,Ouellet, Stephane G.
, p. 83 - 86 (2007/10/03)
(matrix presented) 2-Vinyloxiranes have been found to be excellent surrogates to β,γ-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)3, are effectively tr
