Abstract
An organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols via Michael/acetalization sequence to give fully substituted tetrahydropyranols is described. The process affords the products with high to excellent stereoselectivities (up to 19.9:1.5:1 dr and 98% ee). The highly enantioenriched, less reactive (S)-nitroallylic alcohols 3 were isolated with good to high chemical yields (30-44%). The synthetic application of the resolved substrate is shown toward the synthesis of enantioenriched (+)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid.
| Original language | English |
|---|---|
| Pages (from-to) | 430-433 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 17 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2015 Feb 6 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Control of five contiguous stereogenic centers in an organocatalytic kinetic resolution via michael/acetalization sequence : Synthesis of fully substituted tetrahydropyranols. / Gurubrahamam, Ramani; Cheng, You Song; Chen, Kwunmin.
In: Organic Letters, Vol. 17, No. 3, 06.02.2015, p. 430-433.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Control of five contiguous stereogenic centers in an organocatalytic kinetic resolution via michael/acetalization sequence
T2 - Synthesis of fully substituted tetrahydropyranols
AU - Gurubrahamam, Ramani
AU - Cheng, You Song
AU - Chen, Kwunmin
PY - 2015/2/6
Y1 - 2015/2/6
N2 - An organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols via Michael/acetalization sequence to give fully substituted tetrahydropyranols is described. The process affords the products with high to excellent stereoselectivities (up to 19.9:1.5:1 dr and 98% ee). The highly enantioenriched, less reactive (S)-nitroallylic alcohols 3 were isolated with good to high chemical yields (30-44%). The synthetic application of the resolved substrate is shown toward the synthesis of enantioenriched (+)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid.
AB - An organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols via Michael/acetalization sequence to give fully substituted tetrahydropyranols is described. The process affords the products with high to excellent stereoselectivities (up to 19.9:1.5:1 dr and 98% ee). The highly enantioenriched, less reactive (S)-nitroallylic alcohols 3 were isolated with good to high chemical yields (30-44%). The synthetic application of the resolved substrate is shown toward the synthesis of enantioenriched (+)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid.
UR - http://www.scopus.com/inward/record.url?scp=84922640433&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84922640433&partnerID=8YFLogxK
U2 - 10.1021/ol5033656
DO - 10.1021/ol5033656
M3 - Article
C2 - 25569137
AN - SCOPUS:84922640433
VL - 17
SP - 430
EP - 433
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 3
ER -