155366-63-5Relevant articles and documents
Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by prins cyclization
Ogawa, Yasuyuki,Painter, Phillip P.,Tantillo, Dean J.,Wender, Paul A.
, p. 104 - 115 (2013/03/29)
The Prins cyclization of syn-β-hydroxy allylsilanes and aldehydes gives cis-2,6-disubstituted 4-alkylidenetetrahydropyrans as sole products in excellent yields regardless of the aldehyde (R) or syn-β-hydroxy allylsilane substituent (R) used. By reversing the R and R groups, complementary exocyclic stereocontrol can be achieved. When the anti-β-hydroxy allylsilanes are used, the Prins cyclization gives predominantly cis-2,6-disubstituted 4-alkylidenetetrahydropyrans, now with the opposite olefin geometry in excellent yield. The proposed reaction mechanism and the observed stereoselectivity for these processes are supported by DFT calculations.
Highly Stereoselective Access to 2,4- and 2,4,5-Substituted Tetrahydrofurans from α-Silylacetic Esters. A Study of Homoallylic Stereocontrol.
Andrey, Olivier,Landais, Yannick
, p. 8435 - 8438 (2007/10/02)
Cis-2,4- and cis-cis-2,4,5-substituted tetrahydrofurans have been prepared stereoselectively using electrophile-mediated cyclization of β-hydroxyhomoallylsilanes, readily available from α-silylacetic esters.
