Abstract
Methyltin trichloride and indium(III) chloride promote the addition of aldehydes to cyclic allylic stannanes providing good yields of the corresponding homoallylic alcohols. These reactions proceed via an initial transmetallation involving anti approach of the electrophile, followed by syn aldehyde addition that is erythro selective. These Lewis acids do not promote the corresponding addition of imines, rather providing the same homoallylic alcohols after an in situ aqueous hydrolysis. Imine addition is possible with boron trifluoride-diethyl ether as the Lewis acid.
| Original language | English |
|---|---|
| Pages (from-to) | 957-962 |
| Number of pages | 6 |
| Journal | Journal of the Chemical Society. Perkin Transactions 2 |
| Volume | 2000 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 1 May 2000 |
| Externally published | Yes |
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Aldehyde addition to allylic stannanes via a transmetallation pathway : Stereocontrol in the absence of internal coordination. / Marshall, Raymond L.; Muderawan, I. Wayan; Young, David J.
In: Journal of the Chemical Society. Perkin Transactions 2, Vol. 2000, No. 5, 01.05.2000, p. 957-962.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Aldehyde addition to allylic stannanes via a transmetallation pathway
T2 - Stereocontrol in the absence of internal coordination
AU - Marshall, Raymond L.
AU - Muderawan, I. Wayan
AU - Young, David J.
PY - 2000/5/1
Y1 - 2000/5/1
N2 - Methyltin trichloride and indium(III) chloride promote the addition of aldehydes to cyclic allylic stannanes providing good yields of the corresponding homoallylic alcohols. These reactions proceed via an initial transmetallation involving anti approach of the electrophile, followed by syn aldehyde addition that is erythro selective. These Lewis acids do not promote the corresponding addition of imines, rather providing the same homoallylic alcohols after an in situ aqueous hydrolysis. Imine addition is possible with boron trifluoride-diethyl ether as the Lewis acid.
AB - Methyltin trichloride and indium(III) chloride promote the addition of aldehydes to cyclic allylic stannanes providing good yields of the corresponding homoallylic alcohols. These reactions proceed via an initial transmetallation involving anti approach of the electrophile, followed by syn aldehyde addition that is erythro selective. These Lewis acids do not promote the corresponding addition of imines, rather providing the same homoallylic alcohols after an in situ aqueous hydrolysis. Imine addition is possible with boron trifluoride-diethyl ether as the Lewis acid.
UR - http://www.scopus.com/inward/record.url?scp=0034191472&partnerID=8YFLogxK
U2 - 10.1039/B000435I
DO - 10.1039/B000435I
M3 - Article
VL - 2000
SP - 957
EP - 962
JO - Journal of the Chemical Society. Perkin Transactions 2
JF - Journal of the Chemical Society. Perkin Transactions 2
SN - 0300-9580
IS - 5
ER -