Abstract
The addition of CH3SnCl3 to isomeric mixtures of allylstannane (1) proceeds stereospecifically with anti approach of the electrophile in CD2Cl2 at -78°C but is less selective in CDCl3 at room temperature. The corresponding reaction of crotyltrimethylstannane (CD2Cl2, -78°C) indicates initial γ attack. Addition of CH3SnCl3 to allyltributylstannane (CDCl3,r.t.) followed by benzaldehyde and water hydrolysis yields the expected honoallyl alcohol quantitatively.
| Original language | English |
|---|---|
| Pages (from-to) | 2369-2370 |
| Number of pages | 2 |
| Journal | Tetrahedron Letters |
| Volume | 33 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 17 Apr 1992 |
| Externally published | Yes |
Fingerprint
Cite this
}
The stereochemistry of transmetallation between allylstannanes and CH3SnCl3. / Marshall, Raymond L.; Young, David J.
In: Tetrahedron Letters, Vol. 33, No. 17, 17.04.1992, p. 2369-2370.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - The stereochemistry of transmetallation between allylstannanes and CH3SnCl3
AU - Marshall, Raymond L.
AU - Young, David J.
PY - 1992/4/17
Y1 - 1992/4/17
N2 - The addition of CH3SnCl3 to isomeric mixtures of allylstannane (1) proceeds stereospecifically with anti approach of the electrophile in CD2Cl2 at -78°C but is less selective in CDCl3 at room temperature. The corresponding reaction of crotyltrimethylstannane (CD2Cl2, -78°C) indicates initial γ attack. Addition of CH3SnCl3 to allyltributylstannane (CDCl3,r.t.) followed by benzaldehyde and water hydrolysis yields the expected honoallyl alcohol quantitatively.
AB - The addition of CH3SnCl3 to isomeric mixtures of allylstannane (1) proceeds stereospecifically with anti approach of the electrophile in CD2Cl2 at -78°C but is less selective in CDCl3 at room temperature. The corresponding reaction of crotyltrimethylstannane (CD2Cl2, -78°C) indicates initial γ attack. Addition of CH3SnCl3 to allyltributylstannane (CDCl3,r.t.) followed by benzaldehyde and water hydrolysis yields the expected honoallyl alcohol quantitatively.
UR - http://www.scopus.com/inward/record.url?scp=0026573431&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)74214-6
DO - 10.1016/S0040-4039(00)74214-6
M3 - Article
VL - 33
SP - 2369
EP - 2370
JO - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry
JF - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry
SN - 0040-4039
IS - 17
ER -