Abstract
A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.
| Original language | English |
|---|---|
| Pages (from-to) | 8783-8786 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 37 |
| Issue number | 48 |
| DOIs | |
| Publication status | Published - 1996 Nov 25 |
| Externally published | Yes |
Fingerprint
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction. / Shibata, Takanori; Morioka, Hiroshi; Tanji, Shigehisa; Hayase, Tadakatsu; Kodaka, Yasutaka; Soai, Kenso.
In: Tetrahedron Letters, Vol. 37, No. 48, 25.11.1996, p. 8783-8786.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction
AU - Shibata, Takanori
AU - Morioka, Hiroshi
AU - Tanji, Shigehisa
AU - Hayase, Tadakatsu
AU - Kodaka, Yasutaka
AU - Soai, Kenso
PY - 1996/11/25
Y1 - 1996/11/25
N2 - A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.
AB - A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.
UR - http://www.scopus.com/inward/record.url?scp=0030602193&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030602193&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(96)02031-X
DO - 10.1016/S0040-4039(96)02031-X
M3 - Article
AN - SCOPUS:0030602193
VL - 37
SP - 8783
EP - 8786
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 48
ER -