A new chiral oxathiane: Synthesis, resolution and absolute configuration determination by vibrational circular dichroism

A. Solladié-Cavallo; M. Balaz; M. Salisova; C. Suteu; L. A. Nafie; X. Cao; T. B. Freedman

doi:10.1016/S0957-4166(01)00441-4

A new chiral oxathiane: Synthesis, resolution and absolute configuration determination by vibrational circular dichroism

A. Solladié-Cavallo, M. Balaz, M. Salisova, C. Suteu, L. A. Nafie, X. Cao, T. B. Freedman

Integrated Sciences and Engineering Division

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

A new oxathiane, derived from 5-hydroxy-1-tetralone has been synthesized in eight steps, fully characterized as cis-fused rings by 1D and 2D NMR and resolved by preparative chiral chomatography (CHIRALCEL OD-R). The second eluting (+, MeOH)-isomer was assigned (S,S)-configuration by VCD-ab initio simulation.

Original language	English
Pages (from-to)	2605-2611
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	12
Issue number	18
DOIs	https://doi.org/10.1016/S0957-4166(01)00441-4
Publication status	Published - 2001 Oct 15

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "A new oxathiane, derived from 5-hydroxy-1-tetralone has been synthesized in eight steps, fully characterized as cis-fused rings by 1D and 2D NMR and resolved by preparative chiral chomatography (CHIRALCEL OD-R). The second eluting (+, MeOH)-isomer was assigned (S,S)-configuration by VCD-ab initio simulation.",

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T2 - Synthesis, resolution and absolute configuration determination by vibrational circular dichroism

AU - Solladié-Cavallo, A.

AU - Balaz, M.

AU - Salisova, M.

AU - Suteu, C.

AU - Nafie, L. A.

AU - Cao, X.

AU - Freedman, T. B.

PY - 2001/10/15

Y1 - 2001/10/15

N2 - A new oxathiane, derived from 5-hydroxy-1-tetralone has been synthesized in eight steps, fully characterized as cis-fused rings by 1D and 2D NMR and resolved by preparative chiral chomatography (CHIRALCEL OD-R). The second eluting (+, MeOH)-isomer was assigned (S,S)-configuration by VCD-ab initio simulation.

AB - A new oxathiane, derived from 5-hydroxy-1-tetralone has been synthesized in eight steps, fully characterized as cis-fused rings by 1D and 2D NMR and resolved by preparative chiral chomatography (CHIRALCEL OD-R). The second eluting (+, MeOH)-isomer was assigned (S,S)-configuration by VCD-ab initio simulation.

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JO - Tetrahedron Asymmetry

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