Novel sequential 1, 4-Brook rearrangement–Wittig reaction: new one-pot approach for silyl dienol ethers

Y Matsuya, A Koiwai, D Minato, K Sugimoto…

Index: Matsuya, Yuji; Koiwai, Azusa; Minato, Daishiro; Sugimoto, Kenji; Toyooka, Naoki Tetrahedron Letters, 2012 , vol. 53, # 44 p. 5955 - 5957,3

Full Text: HTML

Citation Number: 9

Abstract

A novel one-pot synthetic method of silyl dienol ethers via 1, 4-Brook rearrangement–Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.

Related Articles:

Base??Catalyzed Cascade 1, 3??H Shift/Cyclization Reaction to Construct Polyaromatic Furans

[Wang, Ya-Hui; Liu, Heng; Zhu, Li-Li; Li, Xiao-Xiao; Chen, Zili Advanced Synthesis and Catalysis, 2011 , vol. 353, # 5 p. 707 - 712]

Lewis base-catalyzed alkynylation of carbonyl compounds with trimethylsilylacetylenes

[Kitazawa, Takayuki; Minowa, Tomofumi; Mukaiyama, Teruaki Chemistry Letters, 2006 , vol. 35, # 9 p. 1002 - 1003]

Lithium Bis-(diisopropylamino) boracetylide [LiC C B (Ni Pr 2) 2]. A new reagent for the preparation of terminal alkynes

[Blanchard, Christiane; Vaultier, Michel; Mortier, Jacques Tetrahedron Letters, 1997 , vol. 38, # 51 p. 8863 - 8866]

Cobaltocene-Induced Low-Temperature Radical Coupling Reactions in a Cobalt–Alkyne Series

[Melikyan, Gagik G.; Rivas, Bianca; Harutyunyan, Stepan; Carlson, Louis; Sepanian, Ruth Organometallics, 2012 , vol. 31, # 5 p. 1653 - 1663]

Chemical Synthesis with Inductively Heated Copper Flow Reactors

[Ceylan, Sascha; Klande, Tobias; Vogt, Carla; Friese, Carsten; Kirschning, Andreas Synlett, 2010 , # 13 p. 2009 - 2013]

More Articles...