Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones

An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin.

We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This method is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

A concise synthesis of tubuphenylalanine and epi-tubuphenylalanine via a diastereoselective Mukaiyama aldol reaction of silyl ketene acetal.

We have developed a straightforward and auxiliary-free synthetic route towards tBu-tubuphenylalanine (tBu-Tup) and tBu-epi-tubuphenylalanine (tBu-epi-Tup), which are the key components of tubulysins and their analogs. A Lewis acid-mediated diastereoselective Mukaiyama aldol reaction using silyl ketene acetal and N-Boc-L-phenylalaninal provided γ-amino-β-hydroxyl-α-methyl esters, which were deox...

Chemoselective silyl transfer in the Mukaiyama aldol reaction promoted by super silyl Lewis acid.

In the silyl Lewis acid-promoted Mukaiyama aldol reaction, the steric and electronic properties of the silyl group on the silyl Lewis acid influence the reaction mechanism and product distribution. When super silyl triflates such as (TMS)3SiOTf and (TES)3SiOTf are used as Lewis acids, the silyl group of the silyl enol ether chemoselectively transfers to the product. The mechanistic details have...

Gallium tribromide catalyzed coupling reaction of alkenyl ethers with ketene silyl acetals.

Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate OSilyl Enolates: A Chiral Tridentate Chelate as a Ligand for Titanium(1V)

Asymmetric catalysis of the Mukaiyama aldol reaction has been reported with complexes derived from Al, B, Sn(II), and Ti(IV).l The levels of asymmetric induction for the addition of propionate-, isobutyrate-, and acetate-derived silyl thioketene acetals to aldehydes parallel those obtained with chiral-auxiliarybased methodologies.2 However, silyl ketene acetals derived from 0-alkyl acetates uni...