Control of five contiguous stereogenic centers in an organocatalytic kinetic resolution via michael/acetalization sequence: Synthesis of fully substituted tetrahydropyranols

Ramani Gurubrahamam, You Song Cheng, Kwunmin Chen

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols via Michael/acetalization sequence to give fully substituted tetrahydropyranols is described. The process affords the products with high to excellent stereoselectivities (up to 19.9:1.5:1 dr and 98% ee). The highly enantioenriched, less reactive (S)-nitroallylic alcohols 3 were isolated with good to high chemical yields (30-44%). The synthetic application of the resolved substrate is shown toward the synthesis of enantioenriched (+)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid.

Original languageEnglish
Pages (from-to)430-433
Number of pages4
JournalOrganic Letters
Volume17
Issue number3
DOIs
Publication statusPublished - 2015 Feb 6

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alcohols
Alcohols
Stereoselectivity
Kinetics
kinetics
synthesis
acids
Substrates
products
3-amino-2-hydroxy-4-phenylbutanoic acid

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Control of five contiguous stereogenic centers in an organocatalytic kinetic resolution via michael/acetalization sequence : Synthesis of fully substituted tetrahydropyranols. / Gurubrahamam, Ramani; Cheng, You Song; Chen, Kwunmin.

In: Organic Letters, Vol. 17, No. 3, 06.02.2015, p. 430-433.

Research output: Contribution to journalArticle

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