Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins

Claire L. Jarvis; Neyra M. Jemal; Spencer Knapp; Daniel Seidel

doi:10.1039/c8ob01015c

Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins

Claire L. Jarvis, Neyra M. Jemal, Spencer Knapp, Daniel Seidel

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

11 Scopus citations

Abstract

A new preparation of δ-lactams is reported. In the presence of a Lewis acid promoter, alkoxyisocoumarins engage a range of N-aryl and N-alkyl imines to form δ-lactams with a pendent carboalkoxy substituent. A sulfonamide-thiourea catalyst enables the synthesis of these products in moderate to good enantioselectivities.

Original language	English (US)
Pages (from-to)	4231-4235
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	23
DOIs	https://doi.org/10.1039/c8ob01015c
State	Published - 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins",

abstract = "A new preparation of δ-lactams is reported. In the presence of a Lewis acid promoter, alkoxyisocoumarins engage a range of N-aryl and N-alkyl imines to form δ-lactams with a pendent carboalkoxy substituent. A sulfonamide-thiourea catalyst enables the synthesis of these products in moderate to good enantioselectivities.",

author = "Jarvis, {Claire L.} and Jemal, {Neyra M.} and Spencer Knapp and Daniel Seidel",

note = "Funding Information: This material is based upon work supported by the National Science Foundation (Grant No. CHE–1565599 to D. S.). S. K. thanks the NIH (Grant No. AI090662) and the Rutgers Aresty program for financial support. Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8ob01015c",

language = "English (US)",

volume = "16",

pages = "4231--4235",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins

AU - Jarvis, Claire L.

AU - Jemal, Neyra M.

AU - Knapp, Spencer

AU - Seidel, Daniel

N1 - Funding Information: This material is based upon work supported by the National Science Foundation (Grant No. CHE–1565599 to D. S.). S. K. thanks the NIH (Grant No. AI090662) and the Rutgers Aresty program for financial support. Publisher Copyright: This journal is © The Royal Society of Chemistry.

PY - 2018

Y1 - 2018

N2 - A new preparation of δ-lactams is reported. In the presence of a Lewis acid promoter, alkoxyisocoumarins engage a range of N-aryl and N-alkyl imines to form δ-lactams with a pendent carboalkoxy substituent. A sulfonamide-thiourea catalyst enables the synthesis of these products in moderate to good enantioselectivities.

AB - A new preparation of δ-lactams is reported. In the presence of a Lewis acid promoter, alkoxyisocoumarins engage a range of N-aryl and N-alkyl imines to form δ-lactams with a pendent carboalkoxy substituent. A sulfonamide-thiourea catalyst enables the synthesis of these products in moderate to good enantioselectivities.

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U2 - 10.1039/c8ob01015c

DO - 10.1039/c8ob01015c

M3 - Article

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AN - SCOPUS:85048630974

SN - 1477-0520

VL - 16

SP - 4231

EP - 4235

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 23

ER -

Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins

Abstract

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