109299-92-5Relevant articles and documents
Total synthesis of (+)-suaveolindole: Establishment of its absolute configuration
Velthuisen, Emile J.,Danishefsky, Samuel J.
, p. 10640 - 10641 (2007)
This communication describes two approaches toward the total synthesis of (+)-suaveolindole. The initial strategy uses a 6-exo-Heck cyclization to generate a transient sp3 carbopalladate. This intermediate was successfully coupled with an indole 3-stannane to assemble the majority of the carbon framework of the natural product. However, due to problems described herein, this interesting route was not viable. To reach our target, lessons learned from the first strategy directed us to develop a significant extension of the Ireland ester enolate rearrangement in which the tetra-substituted isopropylidene group and the α-disposed carboxymethyl function are introduced in a single event. This key reaction enables a remarkably concise inaugural synthesis of (+)-suaveolindole. Copyright
One-pot dehydrogenation of carboxylic acid derivatives to α,β-unsaturated carbonyl compounds under mild conditions
Matsuo, Jun-Ichi,Aizawa, Yayoi
, p. 407 - 410 (2005)
Carboxylic acid derivatives such as N-acyl-2-oxazolidones, δ-lactones, and δ-lactams were smoothly dehydrogenated to the corresponding α,β-unsaturated carbonyl compounds in one-pot manner at -78°C just by treating their lithium enolates with N-tert- butyl
Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives
Lauzon, Samuel,Keipour, Hoda,Gandon, Vincent,Ollevier, Thierry
supporting information, p. 6324 - 6327 (2017/12/08)
A highly enantioselective FeII-catalyzed thia-Michael addition to α,β-unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er). Unusual hepta-coordination of the metal and chelation to α,β-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantioselective event. DFT calculations support the proposed model for observed stereoselectivities.
A protocol for accessing the β-azidation of α,β-unsaturated carboxylic acids
Angelini, Tommaso,Bonollo, Simona,Lanari, Daniela,Pizzo, Ferdinando,Vaccaro, Luigi
supporting information, p. 4610 - 4613 (2012/10/30)
This contribution reports the preparation and use of a new immobilized catalyst, PS-DABCOF (9), which has been specifically designed to access for the first time the efficient β-azidation of α,β-unsaturated carboxylic acids.
