N,O-heterocycles as synthetic intermediates

Roderick W. Bates; Jutatip Boonsombat; Yongna Lu; Joseph A. Nemeth; Kanicha Sa-Ei; Ping Song; Melody Peiling Cai; Philippa B. Cranwell; Sus Ann Winbush

doi:10.1351/pac200880040681

N,O-heterocycles as synthetic intermediates

Roderick W. Bates, Jutatip Boonsombat, Yongna Lu, Joseph A. Nemeth, Kanicha Sa-Ei, Ping Song, Melody Peiling Cai, Philippa B. Cranwell, Sus Ann Winbush

Nanyang Technological University

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

23 Citations (Scopus)

Abstract

Hydroxylamines can be cyclized under various conditions according to the nature of the unsaturation in the N-substituent. Both isoxazolidines and tetrahydrooxazines can be formed with good synthetic control. The choice of the appropriate cyclization reaction leads to syntheses of the natural products sedamine and monomorine. The related N,O-acetals are shown to undergo efficient ring-opening under Sakurai conditions.

Original language	English
Pages (from-to)	681-685
Number of pages	5
Journal	Pure and Applied Chemistry
Volume	80
Issue number	4
DOIs	https://doi.org/10.1351/pac200880040681
Publication status	Published - Apr 2008
Externally published	Yes

ASJC Scopus Subject Areas

General Chemistry
General Chemical Engineering

Keywords

Cyclization
Hydroxylamines
Isoxazolidines
Monomorine
Sakurai conditions
Sedamine
Tetrahydrooxazines

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10.1351/pac200880040681

Cite this

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title = "N,O-heterocycles as synthetic intermediates",

abstract = "Hydroxylamines can be cyclized under various conditions according to the nature of the unsaturation in the N-substituent. Both isoxazolidines and tetrahydrooxazines can be formed with good synthetic control. The choice of the appropriate cyclization reaction leads to syntheses of the natural products sedamine and monomorine. The related N,O-acetals are shown to undergo efficient ring-opening under Sakurai conditions.",

keywords = "Cyclization, Hydroxylamines, Isoxazolidines, Monomorine, Sakurai conditions, Sedamine, Tetrahydrooxazines",

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doi = "10.1351/pac200880040681",

language = "English",

volume = "80",

pages = "681--685",

journal = "Pure and Applied Chemistry",

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TY - JOUR

T1 - N,O-heterocycles as synthetic intermediates

AU - Bates, Roderick W.

AU - Boonsombat, Jutatip

AU - Lu, Yongna

AU - Nemeth, Joseph A.

AU - Sa-Ei, Kanicha

AU - Song, Ping

AU - Cai, Melody Peiling

AU - Cranwell, Philippa B.

AU - Winbush, Sus Ann

PY - 2008/4

Y1 - 2008/4

N2 - Hydroxylamines can be cyclized under various conditions according to the nature of the unsaturation in the N-substituent. Both isoxazolidines and tetrahydrooxazines can be formed with good synthetic control. The choice of the appropriate cyclization reaction leads to syntheses of the natural products sedamine and monomorine. The related N,O-acetals are shown to undergo efficient ring-opening under Sakurai conditions.

AB - Hydroxylamines can be cyclized under various conditions according to the nature of the unsaturation in the N-substituent. Both isoxazolidines and tetrahydrooxazines can be formed with good synthetic control. The choice of the appropriate cyclization reaction leads to syntheses of the natural products sedamine and monomorine. The related N,O-acetals are shown to undergo efficient ring-opening under Sakurai conditions.

KW - Cyclization

KW - Hydroxylamines

KW - Isoxazolidines

KW - Monomorine

KW - Sakurai conditions

KW - Sedamine

KW - Tetrahydrooxazines

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U2 - 10.1351/pac200880040681

DO - 10.1351/pac200880040681

M3 - Article

AN - SCOPUS:42449128839

SN - 0033-4545

VL - 80

SP - 681

EP - 685

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 4

ER -

N,O-heterocycles as synthetic intermediates

Abstract

ASJC Scopus Subject Areas

Keywords

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