ChemInform Abstract: Remote Asymmetric Induction Using Chiral Sulfoxides
β Scribed by Yoshitsugu Arai
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 24 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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Recoverable Chiral Sulfoxide: Remote Asymmetric Induction in Lewis Acid-Promoted Diels-Alder Reaction of Chiral Sulfinyl-Substituted Pyrrolyl Ξ±,Ξ²-Unsaturated Enones. -Stereoselective Diels-Alder reactions in the presence of AlCl 3 or Sm(O-Tf) 3 yield 96-99% of endo-enriched product mixtures which a
The diastereomerically pure sulfinylating reagent (III) reacts with nucleophilic Grignard reagents or the zinc reagent derived from (VI) to yield chiral sulfoxides with excellent yields and enantioselectivities. Under specific conditions sequential reaction of (III) with LiN(Tms)2 followed by aldehy