Synthesis of new, highly hindered C-2-symmetric trans (2S,5S)-disubstituted pyrrolidines

VK Aggarwal; Franck J Sandrinelli; JPH Charmant

Synthesis of new, highly hindered C-2-symmetric trans (2S,5S)-disubstituted pyrrolidines

VK Aggarwal^*, Franck J Sandrinelli, JPH Charmant

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

Abstract

trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Article number	PII S0957-4166(02)00032-0
Pages (from-to)	87-93
Number of pages	7
Journal	Tetrahedron: Asymmetry
Volume	13
Issue number	1
Publication status	Published - 13 Feb 2002

Keywords

DIELS-ALDER REACTION
ALPHA-AMINO-ACIDS
ASYMMETRIC-SYNTHESIS
TRANS-2,5-DISUBSTITUTED PYRROLIDINES
CHIRAL AUXILIARIES
D-MANNITOL
2,5-DISUBSTITUTED PYRROLIDINES
ENANTIOSELECTIVE SYNTHESIS
CLAISEN REARRANGEMENTS
NUCLEOPHILIC-ADDITION

Cite this

@article{c17a5237af7840f0b0d50909aefde08b,

title = "Synthesis of new, highly hindered C-2-symmetric trans (2S,5S)-disubstituted pyrrolidines",

abstract = "trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "DIELS-ALDER REACTION, ALPHA-AMINO-ACIDS, ASYMMETRIC-SYNTHESIS, TRANS-2,5-DISUBSTITUTED PYRROLIDINES, CHIRAL AUXILIARIES, D-MANNITOL, 2,5-DISUBSTITUTED PYRROLIDINES, ENANTIOSELECTIVE SYNTHESIS, CLAISEN REARRANGEMENTS, NUCLEOPHILIC-ADDITION",

author = "VK Aggarwal and Sandrinelli, {Franck J} and JPH Charmant",

year = "2002",

month = feb,

day = "13",

language = "English",

volume = "13",

pages = "87--93",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "1",

}

TY - JOUR

T1 - Synthesis of new, highly hindered C-2-symmetric trans (2S,5S)-disubstituted pyrrolidines

AU - Aggarwal, VK

AU - Sandrinelli, Franck J

AU - Charmant, JPH

PY - 2002/2/13

Y1 - 2002/2/13

N2 - trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.

AB - trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.

KW - DIELS-ALDER REACTION

KW - ALPHA-AMINO-ACIDS

KW - ASYMMETRIC-SYNTHESIS

KW - TRANS-2,5-DISUBSTITUTED PYRROLIDINES

KW - CHIRAL AUXILIARIES

KW - D-MANNITOL

KW - 2,5-DISUBSTITUTED PYRROLIDINES

KW - ENANTIOSELECTIVE SYNTHESIS

KW - CLAISEN REARRANGEMENTS

KW - NUCLEOPHILIC-ADDITION

M3 - Article (Academic Journal)

VL - 13

SP - 87

EP - 93

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

SN - 0957-4166

IS - 1

M1 - PII S0957-4166(02)00032-0

ER -