Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes

Gareth Arnott; Philip C. Bulman Page; Harry Heaney; Roger Hunter; Edward P. Sampler

doi:10.1055/s-2001-11400

Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes

Gareth Arnott, Philip C. Bulman Page, Harry Heaney, Roger Hunter, Edward P. Sampler

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

5 Citations (Scopus)

Abstract

The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C-11 H-23) is reported. The key step makes use of the Mannich reaction for attachment of a chiral diamine-line 2 across the cavity. Yields for this step are good to excellent. One of the bridged compounds exhibits modest activity (27% ee) as an enantioselective catalyst in the addition of diethylzinc to benzaldehyde.

Original language	English
Pages (from-to)	412-414
Number of pages	3
Journal	Synlett
Volume	3
DOIs	https://doi.org/10.1055/s-2001-11400
Publication status	Published - 2001

Keywords

bridged resorcin[4]arene
ACID
ALKYLATION
chiral resorcin[4]arene.
CALIXARENES
Mannich reaction
RESORCARENES
enantioselective catalyst
RING
C-2v-symmetric diamine chiral auxiliary
CALIX<4>RESORCINARENE DERIVATIVES
SELECTIVE DERIVATIZATION
CLOSURE
RESORCINOL
ALDEHYDES

Access to Document

10.1055/s-2001-11400

Cite this

@article{4a233a924c0445e6810634544eb8a1ec,

title = "Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes",

abstract = "The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C-11 H-23) is reported. The key step makes use of the Mannich reaction for attachment of a chiral diamine-line 2 across the cavity. Yields for this step are good to excellent. One of the bridged compounds exhibits modest activity (27% ee) as an enantioselective catalyst in the addition of diethylzinc to benzaldehyde.",

keywords = "bridged resorcin[4]arene, ACID, ALKYLATION, chiral resorcin[4]arene., CALIXARENES, Mannich reaction, RESORCARENES, enantioselective catalyst, RING, C-2v-symmetric diamine chiral auxiliary, CALIX<4>RESORCINARENE DERIVATIVES, SELECTIVE DERIVATIZATION, CLOSURE, RESORCINOL, ALDEHYDES",

author = "Gareth Arnott and {Bulman Page}, {Philip C.} and Harry Heaney and Roger Hunter and Sampler, {Edward P.}",

year = "2001",

doi = "10.1055/s-2001-11400",

language = "English",

volume = "3",

pages = "412--414",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

}

TY - JOUR

T1 - Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes

AU - Arnott, Gareth

AU - Bulman Page, Philip C.

AU - Heaney, Harry

AU - Hunter, Roger

AU - Sampler, Edward P.

PY - 2001

Y1 - 2001

N2 - The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C-11 H-23) is reported. The key step makes use of the Mannich reaction for attachment of a chiral diamine-line 2 across the cavity. Yields for this step are good to excellent. One of the bridged compounds exhibits modest activity (27% ee) as an enantioselective catalyst in the addition of diethylzinc to benzaldehyde.

AB - The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C-11 H-23) is reported. The key step makes use of the Mannich reaction for attachment of a chiral diamine-line 2 across the cavity. Yields for this step are good to excellent. One of the bridged compounds exhibits modest activity (27% ee) as an enantioselective catalyst in the addition of diethylzinc to benzaldehyde.

KW - bridged resorcin[4]arene

KW - ACID

KW - ALKYLATION

KW - chiral resorcin[4]arene.

KW - CALIXARENES

KW - Mannich reaction

KW - RESORCARENES

KW - enantioselective catalyst

KW - RING

KW - C-2v-symmetric diamine chiral auxiliary

KW - CALIX<4>RESORCINARENE DERIVATIVES

KW - SELECTIVE DERIVATIZATION

KW - CLOSURE

KW - RESORCINOL

KW - ALDEHYDES

U2 - 10.1055/s-2001-11400

DO - 10.1055/s-2001-11400

M3 - Article

SN - 0936-5214

VL - 3

SP - 412

EP - 414

JO - Synlett

JF - Synlett

ER -