Abstract
The intramolecular Lewis acid mediated cyclization of γ- alkoxyallylstannanes 1, 2, and 14, bearing a hydrazone group at the terminus of the carbon chain, afforded exclusively the corresponding trans β-amino cyclic ethers 3a, 4a, and 15, respectively. The Lewis acid mediated cyclization of Γ-alkoxyallylstannane 5, having (R)-(+)-1-phenylethylamine as a chiral auxiliary, afforded exclusively, trans ̄-amino cyclic ether 6a with very high diastereomeric excess (de) in very high chemical yields. The asymmetric cyclization of Γ-alkoxyallylstannane with imine 7 in the presence of chiral titanium-BINOL complex 9, afforded predominantly cis β-amino cyclic ether 8b with high enantiomeric excess (ee). The chiral Lewis acid mediated cyclization of racemic compound 38 containing phenyl as a substituent afforded cis isomer 39 with very high enantiomeric excess (ee).
| Original language | English |
|---|---|
| Pages (from-to) | 4901-4908 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 64 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - Jun 25 1999 |
| Externally published | Yes |
Fingerprint
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Diastereo- and enantioselective synthesis of β-amino cyclic ethers via the intramolecular reaction of γ-alkoxyallylstannane with imine. / Park, Jung Youl; Kadota, Isao; Yamamoto, Yoshinori.
In: Journal of Organic Chemistry, Vol. 64, No. 13, 25.06.1999, p. 4901-4908.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diastereo- and enantioselective synthesis of β-amino cyclic ethers via the intramolecular reaction of γ-alkoxyallylstannane with imine
AU - Park, Jung Youl
AU - Kadota, Isao
AU - Yamamoto, Yoshinori
PY - 1999/6/25
Y1 - 1999/6/25
N2 - The intramolecular Lewis acid mediated cyclization of γ- alkoxyallylstannanes 1, 2, and 14, bearing a hydrazone group at the terminus of the carbon chain, afforded exclusively the corresponding trans β-amino cyclic ethers 3a, 4a, and 15, respectively. The Lewis acid mediated cyclization of Γ-alkoxyallylstannane 5, having (R)-(+)-1-phenylethylamine as a chiral auxiliary, afforded exclusively, trans ̄-amino cyclic ether 6a with very high diastereomeric excess (de) in very high chemical yields. The asymmetric cyclization of Γ-alkoxyallylstannane with imine 7 in the presence of chiral titanium-BINOL complex 9, afforded predominantly cis β-amino cyclic ether 8b with high enantiomeric excess (ee). The chiral Lewis acid mediated cyclization of racemic compound 38 containing phenyl as a substituent afforded cis isomer 39 with very high enantiomeric excess (ee).
AB - The intramolecular Lewis acid mediated cyclization of γ- alkoxyallylstannanes 1, 2, and 14, bearing a hydrazone group at the terminus of the carbon chain, afforded exclusively the corresponding trans β-amino cyclic ethers 3a, 4a, and 15, respectively. The Lewis acid mediated cyclization of Γ-alkoxyallylstannane 5, having (R)-(+)-1-phenylethylamine as a chiral auxiliary, afforded exclusively, trans ̄-amino cyclic ether 6a with very high diastereomeric excess (de) in very high chemical yields. The asymmetric cyclization of Γ-alkoxyallylstannane with imine 7 in the presence of chiral titanium-BINOL complex 9, afforded predominantly cis β-amino cyclic ether 8b with high enantiomeric excess (ee). The chiral Lewis acid mediated cyclization of racemic compound 38 containing phenyl as a substituent afforded cis isomer 39 with very high enantiomeric excess (ee).
UR - http://www.scopus.com/inward/record.url?scp=0033603376&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033603376&partnerID=8YFLogxK
U2 - 10.1021/jo9903398
DO - 10.1021/jo9903398
M3 - Article
AN - SCOPUS:0033603376
VL - 64
SP - 4901
EP - 4908
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 13
ER -