Chiral N-Acetyl Selone-Promoted Aldol Reactions

@article{Silks2009ChiralNS,
  title={Chiral N-Acetyl Selone-Promoted Aldol Reactions},
  author={Louis A. “Pete” Silks and David B. Kimball and Duane Michael Hatch and Morgane Ollivault-Shiflett and Ryszard Michalczyk and Eddie W. Moody},
  journal={Synthetic Communications},
  year={2009},
  volume={39},
  pages={641 - 653}
}
Abstract The chiral oxazolidineselone functionality was found to be an excellent partner in the stereospecific acetate aldol reaction with aldehydes via the titanium enolates. Good stereocontrol was obtained as determined by NMR spectroscopy. The oxazolidineselone also provided a straightforward way to establish the stereopurity of the coupling reaction through 77Se NMR spectroscopy. 

Synthesis of a new chiral auxiliary — Non-cross-linked polystyrene-supported oxazolidine-2-selone

A new chiral auxiliary, non-cross-linked polystyrene-supported oxazolidine-2-selone was synthesized using N- Boc-L-tyrosine ethyl ester as starting material. The structure of the target product was

Addition To C=O Bonds III

Samarium Iodide-Promoted Asymmetric Reformatsky Reaction of 3-(2-Haloacyl)-2-oxazolidinones with Enals.

3-(2-Haloacyl)-2-oxazolidinones were shown to react with enals in an asymmetric SmI2-promoted Reformatsky reaction to give stereochemically well-defined 3-hydroxy-4-alkenyl- and

An efficient and one-pot synthesis of 4-aryl-1-thia-3,4a,9-triazafluorene-2-selones

Abstract Reaction between benzoimidazole-2-thiol and aroyl chlorides with potassium selenocyanate in the presence of catalytic amounts of N-methylimidazole under solvent-free conditions provided a

Titanium Enolate Chemistry at the Beginning of the 21st Century

The aim of the microreview is to summarize the current state of knowledge in the field of titanium enolate chemistry. The authors focus on stereoselective organic syntheses promoted by titanium

Stereoselective Acetate Aldol Reactions

The stereochemical control of aldol reactions from unsubstituted enolor enolatelike species, what are known as acetate aldol reactions, has been a matter of concern for nearly 30 years [1, 2].

Synthesis of 4-aryl-7-methoxy-9-thia-[1,3,4a]triazafluorene-2-selones via a three-component condensation of 6-methoxybenzothiazol-2-ylamine, potassium selenocyanate and an acyl chloride

Abstract A simple, one-pot synthesis of six 4-aryl-7-methoxy-9-thia-[1,3,4a]triazafluorene-2-selones has been achieved in moderate to good yields via a three-component condensation of

References

SHOWING 1-10 OF 20 REFERENCES

Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes.

The utility of a valine-derived oxazolidinethione for auxiliary-based asymmetric acetate aldol reactions is reported, with high diastereoselectivity.

Highly Enantioselective Aldol Reaction: Development of a New Chiral Auxiliary from cis-1-Amino-2-hydroxyindan.

Boron enolates obtained from optically active oxazolidinone derivative of cis-1-amino-2-hydroxyindan are reacted with various aldehydes to provide highly enantioselective aldol products in good

Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions.

An indene-based thiazolidinethione chiral auxiliary was prepared in two steps from trans-1-amino-2-indanol and delivered excellent diastereoselectivities in propionate and acetate aldol additions.

Stereoselectivity in aldol reactions of chiral N-acyl selones

A new type of aldol reaction using chiral selone reagents in which the selenocarbonyl plays a pivotal role in determining the stereoselectivity of these reactions.

Highly selective acetate aldol additions using mesityl-substituted chiral auxiliaries.

Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N- acetylthiazolid inethione auxiliaries are reported, and proceed in high yields and diastEREoselectivities for aliphatic, aromatic, and ,-unsaturated aldehydes.

Modern aldol methods for the total synthesis of polyketides.

This Review illustrates by means of selected syntheses of natural products the new variants of the aldol addition, which includes a Aldol additions with various metal enolates, as well as metal-complex-catalyzed, organocatalytic, and biocatalysis methods.

Small organic molecule in enantioselective, direct aldol reaction "in water".

A small organic molecule, Pro-NH(2), catalyzing the enantioselective aldol reaction "in water" not merely "in the presence of water" with good enantioselectivity has been discovered for the first

Determining the solution state orientation of a Ti enolate via stable isotope labeling, NMR spectroscopy, and modeling studies.

Through stable isotope labeling and NMR spectroscopy, this group is able to experimentally observe a Ti enolate in solution and gain insight into its structure and reactivity.