Stereospecific Synthesis of Cyclic Sulfite Esters with Sulfur-Centered Chirality via Diastereoselective Strategy and Intramolecular H‑Bonding Assistance

Stereospecific synthesis of several cyclic sulfite esters containing three stereogenic centers from enantiopure 1,1,4,4-tetraarylbutanetetraols was achieved. Chiral sulfur centers were constructed stereospecifically via a diastereoselective reaction with the assistance of an intramolecular H-bonding...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 1; pp. 379 - 387
Main Authors Hu, Xiaoyun, Yin, Zhongyou, Guo, Jianxin, Adamson, Jasper, Fujiki, Michiya, Borovkov, Victor
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.01.2021
Amer Chemical Soc
Subjects
Online AccessGet full text

Cover

Loading…
More Information
Summary:Stereospecific synthesis of several cyclic sulfite esters containing three stereogenic centers from enantiopure 1,1,4,4-tetraarylbutanetetraols was achieved. Chiral sulfur centers were constructed stereospecifically via a diastereoselective reaction with the assistance of an intramolecular H-bonding interaction. The absolute configuration of the S atom was elucidated by using the corresponding single-crystal X-ray diffraction analysis of the synthesized monochloride cyclic sulfite esters. Furthermore, a crystallographic evidence of the specific intramolecular C­(sp3)–H···CAr weak H-bondings was presented, and its dramatic effect on the 1H NMR spectral properties was revealed. This intriguing behavior was unambiguously rationalized by different shielding effects of the neighboring phenyl rings. Additionally, the theoretical results obtained on the basis of MP2 calculations fully supported the existence of intramolecular hydrogen bonding interactions being responsible for the observed unique chemical and spectral properties.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02147