Journal
ORGANIC LETTERS
Volume 17, Issue 4, Pages 840-843Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol5036613
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Funding
- 100 Talent program of CAS
- National Natural Science Foundation [21272234, 21232001]
- MOST of China [2013CB911501]
- Shenzhen STIC [KQTD201103]
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Employing a chiral spirodiphosphine monoxide ligand with 1,1'-spirobiindane backbone (SDP(O)), a desymmetrization strategy of Pd-catalyzed intramolecular asymmetric aryl C-O coupling of 2-(2-halophenoxy)propane-1,3-diols, was developed. The SDP(O) ligand shows much better results than its SDP counterpart. The protocol provides an efficient and highly enantioselective method for the synthesis of 2-hydroxymethyl-1,4-benzodioxanes. Density functional theory studies provide a model that accounts for the origin of the enantioselectivity.
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