DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CHIRAL SECONDARY ALCOHOLS - NEW ADVANCES USING C-13-NMR AND 2D-NMR SPECTROSCOPY

T  PEHK; E  LIPPMAA; M  LOPP; A  PAJU; B C  BORER; R J K  TAYLOR

DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CHIRAL SECONDARY ALCOHOLS - NEW ADVANCES USING C-13-NMR AND 2D-NMR SPECTROSCOPY

T PEHK, E LIPPMAA, M LOPP, A PAJU, B C BORER, R J K TAYLOR

Chemistry

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

Abstract

The use of H-1-C-13 and H-1-H-1 2D COSY correlation experiments substantially enhances the potential of the NMR procedure for determining the absolute configuration of chiral secondary alcohols via their diastereomeric MPA and/or MTPA esters. Phenyl ring current effects are observed over remarkably long distances and comparable effects are seen for both C-13 and H-1 chemical shifts. The use of C-13 chemical shifts to aid configurational assignment is particularly valuable.

Original language	English
Pages (from-to)	1527-1532
Number of pages	6
Journal	TETRAHEDRON-ASYMMETRY
Volume	4
Issue number	7
Publication status	Published - Jul 1993

Keywords

ENANTIOMERIC PURITY
O-METHYLMANDELATE
CHEMICAL-SHIFTS
MOSHER METHOD
MTPA ESTERS

Cite this

@article{354675c4f14f44598589531f472b0d72,

title = "DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CHIRAL SECONDARY ALCOHOLS - NEW ADVANCES USING C-13-NMR AND 2D-NMR SPECTROSCOPY",

abstract = "The use of H-1-C-13 and H-1-H-1 2D COSY correlation experiments substantially enhances the potential of the NMR procedure for determining the absolute configuration of chiral secondary alcohols via their diastereomeric MPA and/or MTPA esters. Phenyl ring current effects are observed over remarkably long distances and comparable effects are seen for both C-13 and H-1 chemical shifts. The use of C-13 chemical shifts to aid configurational assignment is particularly valuable.",

keywords = "ENANTIOMERIC PURITY, O-METHYLMANDELATE, CHEMICAL-SHIFTS, MOSHER METHOD, MTPA ESTERS",

author = "T PEHK and E LIPPMAA and M LOPP and A PAJU and BORER, {B C} and TAYLOR, {R J K}",

year = "1993",

month = jul,

language = "English",

volume = "4",

pages = "1527--1532",

journal = "TETRAHEDRON-ASYMMETRY",

issn = "0957-4166",

publisher = "Elsevier Ltd.",

number = "7",

}

TY - JOUR

T1 - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CHIRAL SECONDARY ALCOHOLS - NEW ADVANCES USING C-13-NMR AND 2D-NMR SPECTROSCOPY

AU - PEHK, T

AU - LIPPMAA, E

AU - LOPP, M

AU - PAJU, A

AU - BORER, B C

AU - TAYLOR, R J K

PY - 1993/7

Y1 - 1993/7

N2 - The use of H-1-C-13 and H-1-H-1 2D COSY correlation experiments substantially enhances the potential of the NMR procedure for determining the absolute configuration of chiral secondary alcohols via their diastereomeric MPA and/or MTPA esters. Phenyl ring current effects are observed over remarkably long distances and comparable effects are seen for both C-13 and H-1 chemical shifts. The use of C-13 chemical shifts to aid configurational assignment is particularly valuable.

AB - The use of H-1-C-13 and H-1-H-1 2D COSY correlation experiments substantially enhances the potential of the NMR procedure for determining the absolute configuration of chiral secondary alcohols via their diastereomeric MPA and/or MTPA esters. Phenyl ring current effects are observed over remarkably long distances and comparable effects are seen for both C-13 and H-1 chemical shifts. The use of C-13 chemical shifts to aid configurational assignment is particularly valuable.

KW - ENANTIOMERIC PURITY

KW - O-METHYLMANDELATE

KW - CHEMICAL-SHIFTS

KW - MOSHER METHOD

KW - MTPA ESTERS

M3 - Article

SN - 0957-4166

VL - 4

SP - 1527

EP - 1532

JO - TETRAHEDRON-ASYMMETRY

JF - TETRAHEDRON-ASYMMETRY

IS - 7

ER -