Abstract
Bicyclic lactams 14-17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.
Original language | English |
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Pages (from-to) | 2511-2512 |
Number of pages | 2 |
Journal | Journal of the Chemical Society, Chemical Communications |
Issue number | 21 |
DOIs | |
Publication status | Published - 1994 |
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Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones. / Bahajaj, Abood A.; Bailey, Patrick D.; Moore, Madeleine H.; Morgan, Keith M.; Vernon, John M.
In: Journal of the Chemical Society, Chemical Communications, No. 21, 1994, p. 2511-2512.Research output: Contribution to journal › Article
TY - JOUR
T1 - Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones
AU - Bahajaj, Abood A.
AU - Bailey, Patrick D.
AU - Moore, Madeleine H.
AU - Morgan, Keith M.
AU - Vernon, John M.
PY - 1994
Y1 - 1994
N2 - Bicyclic lactams 14-17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.
AB - Bicyclic lactams 14-17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.
UR - http://www.scopus.com/inward/record.url?scp=37049082751&partnerID=8YFLogxK
U2 - 10.1039/C39940002511
DO - 10.1039/C39940002511
M3 - Article
SP - 2511
EP - 2512
JO - Journal of the Chemical Society, Chemical Communications
JF - Journal of the Chemical Society, Chemical Communications
SN - 0022-4936
IS - 21
ER -