Cycloaddition of 5-substituted 1- pyrroline 1-oxide and conversion of the nitrone cycloadducts into cis-and trans- 2,5-disubstituted pyrrolidines

Sk Asrof Ali; Mohammed I.M. Wazeer

doi:10.1016/S0040-4020(01)85751-3

Cycloaddition of 5-substituted 1- pyrroline 1-oxide and conversion of the nitrone cycloadducts into cis-and trans- 2,5-disubstituted pyrrolidines

Sk Asrof Ali^*
, Mohammed I.M. Wazeer

^*Corresponding author for this work

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

52 Scopus citations

Abstract

A study of the regiochemical behaviour of the oxidation of 2-substituted-1-hydroxypyrrolidines (2) being to aldo- and kito-nitrones has been carried out. The mechanism of the peracid induced ring opening reaction of isoxazolidines (5) is now firmly established. Second cycloaddition reaction of 5-substituted 1- pyrroline 1-oxide (6) provides an efficient and stereoselective entry into the trans- (24) as well as cis-2,5- disubstituted pyrrolidines (28).

Original language	English
Pages (from-to)	4339-4354
Number of pages	16
Journal	Tetrahedron
Volume	49
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4020(01)85751-3
State	Published - 1993

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Cycloaddition of 5-substituted 1- pyrroline 1-oxide and conversion of the nitrone cycloadducts into cis-and trans- 2,5-disubstituted pyrrolidines",

abstract = "A study of the regiochemical behaviour of the oxidation of 2-substituted-1-hydroxypyrrolidines (2) being to aldo- and kito-nitrones has been carried out. The mechanism of the peracid induced ring opening reaction of isoxazolidines (5) is now firmly established. Second cycloaddition reaction of 5-substituted 1- pyrroline 1-oxide (6) provides an efficient and stereoselective entry into the trans- (24) as well as cis-2,5- disubstituted pyrrolidines (28).",

author = "Ali, \{Sk Asrof\} and Wazeer, \{Mohammed I.M.\}",

year = "1993",

doi = "10.1016/S0040-4020(01)85751-3",

language = "English",

volume = "49",

pages = "4339--4354",

journal = "Tetrahedron",

issn = "0040-4020",

number = "20",

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T1 - Cycloaddition of 5-substituted 1- pyrroline 1-oxide and conversion of the nitrone cycloadducts into cis-and trans- 2,5-disubstituted pyrrolidines

AU - Ali, Sk Asrof

AU - Wazeer, Mohammed I.M.

PY - 1993

Y1 - 1993

N2 - A study of the regiochemical behaviour of the oxidation of 2-substituted-1-hydroxypyrrolidines (2) being to aldo- and kito-nitrones has been carried out. The mechanism of the peracid induced ring opening reaction of isoxazolidines (5) is now firmly established. Second cycloaddition reaction of 5-substituted 1- pyrroline 1-oxide (6) provides an efficient and stereoselective entry into the trans- (24) as well as cis-2,5- disubstituted pyrrolidines (28).

AB - A study of the regiochemical behaviour of the oxidation of 2-substituted-1-hydroxypyrrolidines (2) being to aldo- and kito-nitrones has been carried out. The mechanism of the peracid induced ring opening reaction of isoxazolidines (5) is now firmly established. Second cycloaddition reaction of 5-substituted 1- pyrroline 1-oxide (6) provides an efficient and stereoselective entry into the trans- (24) as well as cis-2,5- disubstituted pyrrolidines (28).

UR - https://www.scopus.com/pages/publications/0027160531

U2 - 10.1016/S0040-4020(01)85751-3

DO - 10.1016/S0040-4020(01)85751-3

M3 - Article

AN - SCOPUS:0027160531

SN - 0040-4020

VL - 49

SP - 4339

EP - 4354

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

Cycloaddition of 5-substituted 1- pyrroline 1-oxide and conversion of the nitrone cycloadducts into cis-and trans- 2,5-disubstituted pyrrolidines

Abstract

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