PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES

B BURNS; R GRIGG; [No Value] SANTHAKUMAR; Seshadri SRIDHARAN; P STEVENSON; T WORAKUN

PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES

B BURNS
, R GRIGG
, [No Value] SANTHAKUMAR
, Seshadri SRIDHARAN
, P STEVENSON
, T WORAKUN

School of Chemistry and Chemical Engineering

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

121 Citations (Scopus)

Abstract

A new, wide ranging, synthetically powerful, catalytic tandem cyclisation-anion capture process is proposed which depends on the rate of cyclisation of an organopalladium specifies (RPdX) onto a proximate alkene or diene being significantly faster than anion exchange and reductive elimination in the sequence RPdX --> RPdY --> RY + Pd(0). The catalytic cyclisation - anion capture sequence is illustrated for hydride capture by a wide variety of substrates giving rise to fused- and spiro-, carbo- and hetero-cyclic systems, regio- and stereo-specifically.

Original language	English
Pages (from-to)	7297-7320
Number of pages	24
Journal	Tetrahedron
Volume	48
Issue number	35
Publication status	Published - 28 Aug 1992

Keywords

PALLADIUM
CATALYSIS
CYCLIZATION
HYDRIDE CAPTURE
TANDEM PROCESS
METAL-PROMOTED CYCLIZATION
5-EXO-TRIG-VERSUS 6-ENDO-TRIG CYCLIZATIONS
STEREOSELECTIVE TOTAL SYNTHESIS
INTRAMOLECULAR HECK REACTIONS
BIS-EXOCYCLIC DIENES
POLYENE CYCLIZATIONS
CRYSTAL-STRUCTURE
CARBON CENTERS
SILVER-NITRATE
RING-SYSTEMS

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@article{efe19ef67e8845b4a9d72314bdceea75,

title = "PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES",

abstract = "A new, wide ranging, synthetically powerful, catalytic tandem cyclisation-anion capture process is proposed which depends on the rate of cyclisation of an organopalladium specifies (RPdX) onto a proximate alkene or diene being significantly faster than anion exchange and reductive elimination in the sequence RPdX --> RPdY --> RY + Pd(0). The catalytic cyclisation - anion capture sequence is illustrated for hydride capture by a wide variety of substrates giving rise to fused- and spiro-, carbo- and hetero-cyclic systems, regio- and stereo-specifically.",

keywords = "PALLADIUM, CATALYSIS, CYCLIZATION, HYDRIDE CAPTURE, TANDEM PROCESS, METAL-PROMOTED CYCLIZATION, 5-EXO-TRIG-VERSUS 6-ENDO-TRIG CYCLIZATIONS, STEREOSELECTIVE TOTAL SYNTHESIS, INTRAMOLECULAR HECK REACTIONS, BIS-EXOCYCLIC DIENES, POLYENE CYCLIZATIONS, CRYSTAL-STRUCTURE, CARBON CENTERS, SILVER-NITRATE, RING-SYSTEMS",

author = "B BURNS and R GRIGG and SANTHAKUMAR, \{[No Value]\} and Seshadri SRIDHARAN and P STEVENSON and T WORAKUN",

year = "1992",

month = aug,

day = "28",

language = "English",

volume = "48",

pages = "7297--7320",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "35",

}

TY - JOUR

T1 - PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES

AU - BURNS, B

AU - GRIGG, R

AU - SANTHAKUMAR, [No Value]

AU - SRIDHARAN, Seshadri

AU - STEVENSON, P

AU - WORAKUN, T

PY - 1992/8/28

Y1 - 1992/8/28

N2 - A new, wide ranging, synthetically powerful, catalytic tandem cyclisation-anion capture process is proposed which depends on the rate of cyclisation of an organopalladium specifies (RPdX) onto a proximate alkene or diene being significantly faster than anion exchange and reductive elimination in the sequence RPdX --> RPdY --> RY + Pd(0). The catalytic cyclisation - anion capture sequence is illustrated for hydride capture by a wide variety of substrates giving rise to fused- and spiro-, carbo- and hetero-cyclic systems, regio- and stereo-specifically.

AB - A new, wide ranging, synthetically powerful, catalytic tandem cyclisation-anion capture process is proposed which depends on the rate of cyclisation of an organopalladium specifies (RPdX) onto a proximate alkene or diene being significantly faster than anion exchange and reductive elimination in the sequence RPdX --> RPdY --> RY + Pd(0). The catalytic cyclisation - anion capture sequence is illustrated for hydride capture by a wide variety of substrates giving rise to fused- and spiro-, carbo- and hetero-cyclic systems, regio- and stereo-specifically.

KW - PALLADIUM

KW - CATALYSIS

KW - CYCLIZATION

KW - HYDRIDE CAPTURE

KW - TANDEM PROCESS

KW - METAL-PROMOTED CYCLIZATION

KW - 5-EXO-TRIG-VERSUS 6-ENDO-TRIG CYCLIZATIONS

KW - STEREOSELECTIVE TOTAL SYNTHESIS

KW - INTRAMOLECULAR HECK REACTIONS

KW - BIS-EXOCYCLIC DIENES

KW - POLYENE CYCLIZATIONS

KW - CRYSTAL-STRUCTURE

KW - CARBON CENTERS

KW - SILVER-NITRATE

KW - RING-SYSTEMS

M3 - Article

SN - 0040-4020

VL - 48

SP - 7297

EP - 7320

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES

Abstract

Keywords

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