Abstract
The presence of nitrogen atoms in most chiral pharmaceutical drugs has motivated the development of numerous strategies for the synthesis of enantiomerically enriched amines. Current methods are based on multistep transformations of functionalized allylic electrophiles to form chiral allylic amines. The enantioselective allylic amination of nonactivated olefins would represent a more direct and more attractive strategy. We report the enantio selective synthesis of ent-sitagliptin through an allylic amination of a nonactivated terminal olefin.
| Original language | English (US) |
|---|---|
| Article number | ST-2013-S0710-L |
| Pages (from-to) | 2459-2463 |
| Number of pages | 5 |
| Journal | Synlett |
| Volume | 24 |
| Issue number | 18 |
| DOIs | |
| State | Published - 2013 |
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Keywords
- aminations
- asymmetric catalysis
- drugs
- palladium
- rearrangements
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Catalytic enantioselective allylic amination of olefins for the synthesis of ent -sitagliptin. / Bao, Hongli; Bayeh, Liela; Tambar, Uttam.
In: Synlett, Vol. 24, No. 18, ST-2013-S0710-L, 2013, p. 2459-2463.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Catalytic enantioselective allylic amination of olefins for the synthesis of ent -sitagliptin
AU - Bao, Hongli
AU - Bayeh, Liela
AU - Tambar, Uttam
PY - 2013
Y1 - 2013
N2 - The presence of nitrogen atoms in most chiral pharmaceutical drugs has motivated the development of numerous strategies for the synthesis of enantiomerically enriched amines. Current methods are based on multistep transformations of functionalized allylic electrophiles to form chiral allylic amines. The enantioselective allylic amination of nonactivated olefins would represent a more direct and more attractive strategy. We report the enantio selective synthesis of ent-sitagliptin through an allylic amination of a nonactivated terminal olefin.
AB - The presence of nitrogen atoms in most chiral pharmaceutical drugs has motivated the development of numerous strategies for the synthesis of enantiomerically enriched amines. Current methods are based on multistep transformations of functionalized allylic electrophiles to form chiral allylic amines. The enantioselective allylic amination of nonactivated olefins would represent a more direct and more attractive strategy. We report the enantio selective synthesis of ent-sitagliptin through an allylic amination of a nonactivated terminal olefin.
KW - aminations
KW - asymmetric catalysis
KW - drugs
KW - palladium
KW - rearrangements
UR - http://www.scopus.com/inward/record.url?scp=84885758870&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84885758870&partnerID=8YFLogxK
U2 - 10.1055/s-0033-1340079
DO - 10.1055/s-0033-1340079
M3 - Article
C2 - 25378809
AN - SCOPUS:84885758870
VL - 24
SP - 2459
EP - 2463
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 18
M1 - ST-2013-S0710-L
ER -