Abstract
We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.
| Original language | English |
|---|---|
| Pages (from-to) | 1360-1363 |
| Number of pages | 4 |
| Journal | Chemistry Letters |
| Volume | 47 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - Jan 1 2018 |
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Keywords
- 1 3-Diol
- Chiral DMAP derivative
- Desymmetrization
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative. / Mandai, Hiroki; Ashihara, Kosuke; Mitsudo, Koichi; Suga, Seiji.
In: Chemistry Letters, Vol. 47, No. 11, 01.01.2018, p. 1360-1363.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative
AU - Mandai, Hiroki
AU - Ashihara, Kosuke
AU - Mitsudo, Koichi
AU - Suga, Seiji
PY - 2018/1/1
Y1 - 2018/1/1
N2 - We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.
AB - We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.
KW - 1 3-Diol
KW - Chiral DMAP derivative
KW - Desymmetrization
UR - http://www.scopus.com/inward/record.url?scp=85054816995&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85054816995&partnerID=8YFLogxK
U2 - 10.1246/cl.180697
DO - 10.1246/cl.180697
M3 - Article
VL - 47
SP - 1360
EP - 1363
JO - Chemistry Letters
JF - Chemistry Letters
SN - 0366-7022
IS - 11
ER -