2129-95-5Relevant articles and documents
Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes
Steinreiber, Andreas,Mayer, Sandra F.,Saf, Robert,Faber, Kurt
, p. 1519 - 1528 (2001)
Asymmetric biohydrolysis of trialkyl oxiranes (±)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols 1b-3b in up to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence was investigated by 18O-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity.
A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes
Bahou, Karim A.,Braddock, D. Christopher,Meyer, Adam G.,Savage, G. Paul,Shi, Zhensheng,He, Tianyou
, p. 4906 - 4917 (2020/04/10)
A retrosynthetic disconnection-reconnection analysis of epoxypolyenes - substrates that can undergo cyclization to podocarpane-type tricycles - reveals relay-actuated Δ6,7-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross-metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (E/Z, ca. 2-3:1). The method is further generalized for the cross-metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ6,7-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the E-geometrical isomer).
Alkylation of 2-substituted (6-Methyl-2-pyridyl)methyllithium species with epoxides
Vyvyan, James R.,Brown, Rebecca C.,Woods, Brian P.
supporting information; experimental part, p. 1374 - 1376 (2009/07/04)
Substituted (6-methyl-2-pyridyl)methyllithium species were reacted with 1,2-epoxyoctane and 2-methyl-2,3-epoxynonane. The monosubstituted epoxide reacted efficiently with lutidyllithium and a number of 2-substituted (6-methyl-2-pyridyl)methyllithium deriv