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- Title
Efficient and Easy Access to Optically Pure Tetrasubstituted Tetrahydrofurans via Stereoselective Opening of C<sub>2</sub>-Symmetric Epoxide and Aziridine Rings.
- Authors
Kumar Kondapi, Venkata Pavan; Soueidan, Olivier‐Mohamad; Hosseini, Seyedeh Nargess; Jabari, Nauras; West, Frederick G.
- Abstract
An efficient and facile protocol to functionalize position C-3 of 2,5-anhydro- D-mannitol via diastereoselective ring opening of a C2-symmetric epoxide 2,5:3,4-dianhydro- D-allitol 3 has been developed. This method is protecting-group-free, high-yielding, and provides access to C-3-modified 2,5-anhydro- D-mannitols 5a, 11a- 15a and 16- 17. This method was then extrapolated to the synthesis of a C2-symmetric aziridine, which underwent ring opening with various nucleophiles to provide access to C-3- and C-4-modified 2,5-anhydro- D-mannitols 19- 27 in excellent global yields and moderate to good diastereoselectivities. These structures and their derivatives are potentially useful in a variety of applications, including organocatalysis of asymmetric Michael additions as demonstrated with diamine monosulfonamides 28a and 28b, which provide adducts with complementary enantioselectivity.
- Subjects
EPOXY compounds; AZIRIDINES; MANNITOL; NUCLEOPHILES; MICHAEL reaction; SULFONAMIDES
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 7, p1367
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201501540