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Tetrahedron Letters

Volumn 43, Issue 28, 2002, Pages 4931-4933

An asymmetric synthesis of a 4-substituted-1,4-dihydropyridine

(5) Ashworth, Ian a Hopes, Phillip b Levin, Danny b Patel, Ian b Salloo, Rashida a

a JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE (United Kingdom)

b ASTRAZENECA (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYIDINE; DIHYDROPYRIDINE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CRYSTALLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; MICHAEL ADDITION; STEREOCHEMISTRY; URINE INCONTINENCE;

EID: 0037043058 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(02)00975-9 Document Type: Article

Times cited : (35)

References (15)

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- Internal report: ZD0947 Technology Transfer Document, K. Russell, May 1998

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5
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8
- 0000889920
- (1994) Heterocycles , vol.39 , pp. 591-602
- Kosugi, Y.¹ Hori, M.² Tatsuo, N.³

9
- 0005989456
- See Ref. 8 and those cited within

10
- 0026561424
- (1992) Tetrahedron: Asymmetry , vol.3 , pp. 459-505
- D'Angelo, J.¹ Desmaele, D.² Dumas, F.³ Guingant, A.⁴

11
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- PCT/SE01/01 685 and PCT/SE01/01686
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- 0031949090
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13
- 0000408807
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14
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- A complex mixture of diastereoisomers is produced and an absolute figure for diastereoselectivity has not been found. However, a correlation of the ratio of the peaks in the HPLC on analysis of 10 when compared to the enantiomeric excess of the crude reaction mixture of 1 can be drawn, and thus the ratio can be reported to be approximately 70% d.e. This is enhanced to greater than 95% e.e. following isolation of 1 as compared to reference materials and analysis by chiral HPLC (Chiralpak AD, 25 cm×4.6 mm)

15
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- The isolated compound is consistent with reference spectra (NMR and MS)

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