Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements

Stephen G. Davies; A. Christopher Garner; Rebecca L. Nicholson; James Osborne; Edward D. Savory; Andrew D. Smith

doi:10.1039/b306323m

Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements

Stephen G. Davies^*
, A. Christopher Garner
, Rebecca L. Nicholson
, James Osborne
, Edward D. Savory
, Andrew D. Smith

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	2134-2135
Number of pages	2
Journal	Chemical Communications
Volume	3
Issue number	17
DOIs	https://doi.org/10.1039/b306323m
Publication status	Published - 1 Jan 2003

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@article{53b24230f2c34daab4f06737317d8349,

title = "Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements",

abstract = "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.",

author = "Davies, \{Stephen G.\} and Garner, \{A. Christopher\} and Nicholson, \{Rebecca L.\} and James Osborne and Savory, \{Edward D.\} and Smith, \{Andrew D.\}",

year = "2003",

month = jan,

day = "1",

doi = "10.1039/b306323m",

language = "English",

volume = "3",

pages = "2134--2135",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "17",

}

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 - https://www.scopus.com/pages/publications/0042235221

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 -

Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements

Abstract

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