132816-01-4Relevant academic research and scientific papers
1,3-Asymmetric Induction in Diastereoselective Allylations of Chiral N-Tosyl Imines
Fettinger, James C.,Gutierrez, David A.,Lo, Anna,Shaw, Jared T.,Toth-Williams, Garrett
, (2022/02/07)
Lewis acid mediated allylations of β-alkoxy N-tosyl imines using allyltrimethylsilane lead to 3-alkoxy homoallylic N-tosyl amines with anti-selectivity. Two methods of Cu(OTf)2-mediated allylations are reported herein, demonstrating that diastereoselectiv
Sc(OTf)3-Catalyzed Addition of Bromomagnesium 2-Vinyloxy Ethoxide to Various Aldehydes Leading to Protected Aldol Products
Quinio, Pauline,Kohout, Laura,Roman, Daniela Sustac,Gaar, Jakob,Karaghiosoff, Konstantin,Knochel, Paul
, p. 1715 - 1719 (2016/07/06)
The addition of bromomagnesium 2-vinyloxy ethoxide to various aldehydes in the presence of 10 mol% Sc(OTf)3 provides a broad range of functionalized protected aldol compounds. The enantioselective preparation of these aldols can be achieved via a Swern oxidation-CBS reduction sequence. Use of the dioxolane derived from 2-bromocyclohexanone provides the expected aldol product as the anti diastereoisomer (dr >99:1).
Enantioselective allyltitanations and metathesis reactions. Application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline
Cossy, Janine,Willis, Catherine,Bellosta, Veronique,BouzBouz, Samir
, p. 1982 - 1992 (2007/10/03)
An enantioselective synthesis of the piperidine alkaloids (+)-sedamine and (-)-prosophylline is reported. The synthesis of (+)-sedamine has been achieved in 12 steps with an overall yield of 20% from benzaldehyde, and (-)-prosophylline was obtained in 15 steps with an overall yield of 9.2%, starting from D-glyceraldehyde acetonide 14. The key steps are enantioselective allyltitanation reactions and ring-closing or cross-metathesis reactions.
Asymmetric Induction in Reductively Initiated -Wittig and Retro -Brook Rearrangements of Secondary Carbanions
Hoffmann, Rolf,Brueckner, Reinhard
, p. 1471 - 1484 (2007/10/02)
The synthesis of O,S-acetals and the lithium naphthalenide initiated rearrangement reactions thereof are described.O,S-Acetal 8a resulted from trapping of the 1,4-dipole 7 with thiophenol.O,S-Acetals 16a and b were obtained from aldehydes 14a/b by a one-p
