EFFICIENT SYNTHESIS OF 3-SUBSTITUTED LACTAMS USING MEERWEIN ESCHENMOSER CLAISEN [3,3] SIGMATROPIC REARRANGEMENTS

B COATES; D MONTGOMERY; PJ STEVENSON; Paul Stevenson

EFFICIENT SYNTHESIS OF 3-SUBSTITUTED LACTAMS USING MEERWEIN ESCHENMOSER CLAISEN [3,3] SIGMATROPIC REARRANGEMENTS

B COATES
, D MONTGOMERY
, PJ STEVENSON
, Paul Stevenson

School of Chemistry and Chemical Engineering

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

15 Citations (Scopus)

Abstract

3-Allyl substituted five, six, and seven membered ring lactams are readily available in good yields and reasonable selectivity by a formal Meerwein Eschenmoser Claisen [3,3] rearrangement, using the readily available N,N-dialkylalkoxymethylene iminium salts and lithium alkoxides derived from allyl alcohols.

Original language	English
Pages (from-to)	4199-4202
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	33
Publication status	Published - 12 Aug 1991

Keywords

[3,3] SIGMATROPIC REARRANGEMENT
3-SUBSTITUTED LACTAMS
QUARTERNARY CHIRAL CENTERS
STEREOCHEMICAL CONTROL

Cite this

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title = "EFFICIENT SYNTHESIS OF 3-SUBSTITUTED LACTAMS USING MEERWEIN ESCHENMOSER CLAISEN [3,3] SIGMATROPIC REARRANGEMENTS",

abstract = "3-Allyl substituted five, six, and seven membered ring lactams are readily available in good yields and reasonable selectivity by a formal Meerwein Eschenmoser Claisen [3,3] rearrangement, using the readily available N,N-dialkylalkoxymethylene iminium salts and lithium alkoxides derived from allyl alcohols.",

keywords = "[3,3] SIGMATROPIC REARRANGEMENT, 3-SUBSTITUTED LACTAMS, QUARTERNARY CHIRAL CENTERS, STEREOCHEMICAL CONTROL",

author = "B COATES and D MONTGOMERY and PJ STEVENSON and Paul Stevenson",

year = "1991",

month = aug,

day = "12",

language = "English",

volume = "32",

pages = "4199--4202",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "33",

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TY - JOUR

T1 - EFFICIENT SYNTHESIS OF 3-SUBSTITUTED LACTAMS USING MEERWEIN ESCHENMOSER CLAISEN [3,3] SIGMATROPIC REARRANGEMENTS

AU - COATES, B

AU - MONTGOMERY, D

AU - STEVENSON, PJ

AU - Stevenson, Paul

PY - 1991/8/12

Y1 - 1991/8/12

N2 - 3-Allyl substituted five, six, and seven membered ring lactams are readily available in good yields and reasonable selectivity by a formal Meerwein Eschenmoser Claisen [3,3] rearrangement, using the readily available N,N-dialkylalkoxymethylene iminium salts and lithium alkoxides derived from allyl alcohols.

AB - 3-Allyl substituted five, six, and seven membered ring lactams are readily available in good yields and reasonable selectivity by a formal Meerwein Eschenmoser Claisen [3,3] rearrangement, using the readily available N,N-dialkylalkoxymethylene iminium salts and lithium alkoxides derived from allyl alcohols.

KW - [3,3] SIGMATROPIC REARRANGEMENT

KW - 3-SUBSTITUTED LACTAMS

KW - QUARTERNARY CHIRAL CENTERS

KW - STEREOCHEMICAL CONTROL

M3 - Article

SN - 0040-4039

VL - 32

SP - 4199

EP - 4202

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

EFFICIENT SYNTHESIS OF 3-SUBSTITUTED LACTAMS USING MEERWEIN ESCHENMOSER CLAISEN [3,3] SIGMATROPIC REARRANGEMENTS

Abstract

Keywords

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