Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine

Stephen G. Davies; Keiji Iwamoto; Christian A.P. Smethurst; Andrew D. Smith; Humberto Rodriguez-Solla

Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine

Stephen G. Davies^*, Keiji Iwamoto, Christian A.P. Smethurst, Andrew D. Smith, Humberto Rodriguez-Solla

^*Corresponding author for this work

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

Abstract

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.

Original language	English
Pages (from-to)	1146-1148
Number of pages	3
Journal	Synlett
Issue number	7
Publication status	Published - 25 Jul 2002

Keywords

Asymmetric synthesis
Conjugate addition
Cyclic β-amino acids
Lithium amide
Ring closing metathesis

Cite this

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title = "Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine",

abstract = "Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.",

keywords = "Asymmetric synthesis, Conjugate addition, Cyclic β-amino acids, Lithium amide, Ring closing metathesis",

author = "Davies, \{Stephen G.\} and Keiji Iwamoto and Smethurst, \{Christian A.P.\} and Smith, \{Andrew D.\} and Humberto Rodriguez-Solla",

year = "2002",

month = jul,

day = "25",

language = "English",

pages = "1146--1148",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "7",

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TY - JOUR

T1 - Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine

AU - Davies, Stephen G.

AU - Iwamoto, Keiji

AU - Smethurst, Christian A.P.

AU - Smith, Andrew D.

AU - Rodriguez-Solla, Humberto

PY - 2002/7/25

Y1 - 2002/7/25

N2 - Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.

AB - Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.

KW - Asymmetric synthesis

KW - Conjugate addition

KW - Cyclic β-amino acids

KW - Lithium amide

KW - Ring closing metathesis

UR - https://www.scopus.com/pages/publications/0036070055

M3 - Article

AN - SCOPUS:0036070055

SN - 0936-5214

SP - 1146

EP - 1148

JO - Synlett

JF - Synlett

IS - 7

ER -

Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine

Abstract

Keywords

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