Multi-component reactions of 2-isopropylidene-aziridines: application to the synthesis of enantiopure neopentylamines

JF Hayes; M Shipman; Alexandra Martha Zoya Slawin; H Twin

Multi-component reactions of 2-isopropylidene-aziridines: application to the synthesis of enantiopure neopentylamines

JF Hayes
, M Shipman
, Alexandra Martha Zoya Slawin
, H Twin

Research output: Other contribution

Abstract

Neopentylamines {(1S,1'S)-7a,b} are made from (S)-2isopropylidene-1-(1-phenylethyl)aziridine (4) in 73% and 56% yields respectively, and as single diastereomers, using a multi-component reaction (M-CR). The structure of (1S,1'S)-7a is confirmed by X-Ray crystallography. Cleavage of the chiral control element {(S)-PhMeCH} from 7a yields neopentyl type amine (8(.)HCl) (greater than or equal to95%ee). Further experiments reveal the scope and limitations of this M-CR.

Original language	English
Volume	58
Publication status	Published - 22 Nov 2002

Keywords

amine
aziridine
stereocontrol
RING-OPENING REACTIONS
2-METHYLENEAZIRIDINES
BOND

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@misc{9e2707f6e8894095a7b7af90d51c3d03,

title = "Multi-component reactions of 2-isopropylidene-aziridines: application to the synthesis of enantiopure neopentylamines",

abstract = "Neopentylamines \{(1S,1'S)-7a,b\} are made from (S)-2isopropylidene-1-(1-phenylethyl)aziridine (4) in 73\% and 56\% yields respectively, and as single diastereomers, using a multi-component reaction (M-CR). The structure of (1S,1'S)-7a is confirmed by X-Ray crystallography. Cleavage of the chiral control element \{(S)-PhMeCH\} from 7a yields neopentyl type amine (8(.)HCl) (greater than or equal to95\%ee). Further experiments reveal the scope and limitations of this M-CR.",

keywords = "amine, aziridine, stereocontrol, RING-OPENING REACTIONS, 2-METHYLENEAZIRIDINES, BOND",

author = "JF Hayes and M Shipman and Slawin, \{Alexandra Martha Zoya\} and H Twin",

note = "Heterocycles",

year = "2002",

month = nov,

day = "22",

language = "English",

volume = "58",

type = "Other",

}

TY - GEN

T1 - Multi-component reactions of 2-isopropylidene-aziridines: application to the synthesis of enantiopure neopentylamines

AU - Hayes, JF

AU - Shipman, M

AU - Slawin, Alexandra Martha Zoya

AU - Twin, H

N1 - Heterocycles

PY - 2002/11/22

Y1 - 2002/11/22

N2 - Neopentylamines {(1S,1'S)-7a,b} are made from (S)-2isopropylidene-1-(1-phenylethyl)aziridine (4) in 73% and 56% yields respectively, and as single diastereomers, using a multi-component reaction (M-CR). The structure of (1S,1'S)-7a is confirmed by X-Ray crystallography. Cleavage of the chiral control element {(S)-PhMeCH} from 7a yields neopentyl type amine (8(.)HCl) (greater than or equal to95%ee). Further experiments reveal the scope and limitations of this M-CR.

AB - Neopentylamines {(1S,1'S)-7a,b} are made from (S)-2isopropylidene-1-(1-phenylethyl)aziridine (4) in 73% and 56% yields respectively, and as single diastereomers, using a multi-component reaction (M-CR). The structure of (1S,1'S)-7a is confirmed by X-Ray crystallography. Cleavage of the chiral control element {(S)-PhMeCH} from 7a yields neopentyl type amine (8(.)HCl) (greater than or equal to95%ee). Further experiments reveal the scope and limitations of this M-CR.

KW - amine

KW - aziridine

KW - stereocontrol

KW - RING-OPENING REACTIONS

KW - 2-METHYLENEAZIRIDINES

KW - BOND

UR - https://www.scopus.com/pages/publications/0037159761

M3 - Other contribution

VL - 58

ER -

Multi-component reactions of 2-isopropylidene-aziridines: application to the synthesis of enantiopure neopentylamines

Abstract

Keywords

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