TY - JOUR
T1 - Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements
AU - Davies, Stephen G.
AU - Garner, A. Christopher
AU - Nicholson, Rebecca L.
AU - Osborne, James
AU - Savory, Edward D.
AU - Smith, Andrew D.
PY - 2003/1/1
Y1 - 2003/1/1
N2 - Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N, O-silylketene aminal of (3S,4E,αR)-1-benzyloxy-3-(N-propionyl-N-α-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,αR)-N-α-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in >92% d.e.; rearrangement of the diastereomeric (3R,4E,αR)-(Z)-N, O-silylketene aminal proceeds with low diastereoselectivity.
AB - Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N, O-silylketene aminal of (3S,4E,αR)-1-benzyloxy-3-(N-propionyl-N-α-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,αR)-N-α-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in >92% d.e.; rearrangement of the diastereomeric (3R,4E,αR)-(Z)-N, O-silylketene aminal proceeds with low diastereoselectivity.
UR - http://www.scopus.com/inward/record.url?scp=0042235221&partnerID=8YFLogxK
U2 - 10.1039/b306323m
DO - 10.1039/b306323m
M3 - Article
AN - SCOPUS:0042235221
SN - 1359-7345
VL - 3
SP - 2134
EP - 2135
JO - Chemical Communications
JF - Chemical Communications
IS - 17
ER -