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Published on: July 30, 2017
2,2'-Bis(meth-oxy-meth-oxy)-3-methyl-1,1'-binaphth-yl
Acta Crystallographica. Section E, Structure Reports Online
|November 8, 2011
Summary
This study details a methoxymethyl (MOM) bis-protected BINOL derivative, a crucial intermediate for synthesizing diverse chiral auxiliaries. Its unique structure features naphthyl rings angled at 70.74 degrees, with no intermolecular hydrogen bonds.
Area of Science:
- Organic Chemistry
- Stereochemistry
- Crystallography
Background:
- BINOL derivatives are vital scaffolds in asymmetric synthesis.
- Chiral auxiliaries are essential for controlling stereochemical outcomes.
- Methoxy-methyl (MOM) protection is a common strategy in organic synthesis.
Purpose of the Study:
- To synthesize and characterize a novel MOM bis-protected BINOL derivative.
- To investigate the structural properties of the title compound.
- To highlight its utility as a precursor for chiral auxiliaries.
Main Methods:
- Synthesis of the MOM bis-protected BINOL derivative.
- Single-crystal X-ray diffraction analysis.
- Structural elucidation and conformational analysis.
Main Results:
- The title compound, C(25)H(24)O(4), was successfully synthesized.
- X-ray crystallography revealed the naphthyl rings are oriented at 70.74(3)°.
- No conventional intermolecular hydrogen bonds were observed in the crystal structure.
Conclusions:
- The characterized MOM bis-protected BINOL derivative serves as a valuable building block.
- Its defined stereochemistry and structural features are advantageous for chiral auxiliary development.
- This compound facilitates access to a wide range of enantiomerically pure molecules.
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