HIGHLY DIASTEREOSELECTIVE FUNCTIONALIZATION OF CALIX[4]RESORCINARENE DERIVATIVES AND ACID-CATALYZED EPIMERIZATION REACTIONS

M T  ELGIHANI; H  HEANEY; A M Z  SLAWIN

HIGHLY DIASTEREOSELECTIVE FUNCTIONALIZATION OF CALIX[4]RESORCINARENE DERIVATIVES AND ACID-CATALYZED EPIMERIZATION REACTIONS

M T ELGIHANI, H HEANEY, A M Z SLAWIN

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

Abstract

Mannich reactions of a number of calix[4]resorcinarene derivatives with (R)-(+)-alpha-methylbenzylamine under alkaline conditions lead to the formation of single diastereomeric tetrakis(1,3-dihydrobenzoxazine) derivatives in high yields; the reactions using the (S)-(-)-alpha-methylbenzylamine afford the enantiomers. The products react with protic acids to afford equilibrium mixtures of diastereomers.

Original language	English
Pages (from-to)	4905-4908
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	27
Publication status	Published - 3 Jul 1995

Keywords

HYDROGEN-BONDING INTERACTION
HOST GUEST COMPLEXATION
MOLECULAR RECOGNITION
MANNICH REACTIONS
CALIX<4>ARENES
MACROCYCLE
RESORCINOL
CAVITANDS
ETHERS

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title = "HIGHLY DIASTEREOSELECTIVE FUNCTIONALIZATION OF CALIX[4]RESORCINARENE DERIVATIVES AND ACID-CATALYZED EPIMERIZATION REACTIONS",

abstract = "Mannich reactions of a number of calix[4]resorcinarene derivatives with (R)-(+)-alpha-methylbenzylamine under alkaline conditions lead to the formation of single diastereomeric tetrakis(1,3-dihydrobenzoxazine) derivatives in high yields; the reactions using the (S)-(-)-alpha-methylbenzylamine afford the enantiomers. The products react with protic acids to afford equilibrium mixtures of diastereomers.",

keywords = "HYDROGEN-BONDING INTERACTION, HOST GUEST COMPLEXATION, MOLECULAR RECOGNITION, MANNICH REACTIONS, CALIX<4>ARENES, MACROCYCLE, RESORCINOL, CAVITANDS, ETHERS",

author = "ELGIHANI, {M T} and H HEANEY and SLAWIN, {A M Z}",

year = "1995",

month = jul,

day = "3",

language = "English",

volume = "36",

pages = "4905--4908",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "27",

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TY - JOUR

T1 - HIGHLY DIASTEREOSELECTIVE FUNCTIONALIZATION OF CALIX[4]RESORCINARENE DERIVATIVES AND ACID-CATALYZED EPIMERIZATION REACTIONS

AU - ELGIHANI, M T

AU - HEANEY, H

AU - SLAWIN, A M Z

PY - 1995/7/3

Y1 - 1995/7/3

N2 - Mannich reactions of a number of calix[4]resorcinarene derivatives with (R)-(+)-alpha-methylbenzylamine under alkaline conditions lead to the formation of single diastereomeric tetrakis(1,3-dihydrobenzoxazine) derivatives in high yields; the reactions using the (S)-(-)-alpha-methylbenzylamine afford the enantiomers. The products react with protic acids to afford equilibrium mixtures of diastereomers.

AB - Mannich reactions of a number of calix[4]resorcinarene derivatives with (R)-(+)-alpha-methylbenzylamine under alkaline conditions lead to the formation of single diastereomeric tetrakis(1,3-dihydrobenzoxazine) derivatives in high yields; the reactions using the (S)-(-)-alpha-methylbenzylamine afford the enantiomers. The products react with protic acids to afford equilibrium mixtures of diastereomers.

KW - HYDROGEN-BONDING INTERACTION

KW - HOST GUEST COMPLEXATION

KW - MOLECULAR RECOGNITION

KW - MANNICH REACTIONS

KW - CALIX<4>ARENES

KW - MACROCYCLE

KW - RESORCINOL

KW - CAVITANDS

KW - ETHERS

M3 - Article

SN - 0040-4039

VL - 36

SP - 4905

EP - 4908

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

ER -

HIGHLY DIASTEREOSELECTIVE FUNCTIONALIZATION OF CALIX[4]RESORCINARENE DERIVATIVES AND ACID-CATALYZED EPIMERIZATION REACTIONS

Abstract

Keywords

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