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458570

Sigma-Aldrich

(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one

98%

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About This Item

Empirical Formula (Hill Notation):
C13H13NO2
CAS Number:
Molecular Weight:
215.25
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

assay

98%

optical activity

[α]20/D +124°, c = 1 in chloroform

optical purity

ee: ≥99% (HPLC)

mp

90-92 °C (lit.)

functional group

ether
phenyl

SMILES string

C[C@]12OC[C@@H](N1C(=O)C=C2)c3ccccc3

InChI

1S/C13H13NO2/c1-13-8-7-12(15)14(13)11(9-16-13)10-5-3-2-4-6-10/h2-8,11H,9H2,1H3/t11-,13-/m1/s1

InChI key

UFQSRYWJCHFOQX-DGCLKSJQSA-N

Application

High levels of asymmetric induction[1] have been obtained with this chiral bicyclic lactam in cycloadditions,[2][3] alkylations,[4][5][6] conjugate additions,[7][8] annulations,[9] and dihydroxylations.[10]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Romo, D. Meyers, A.I.
Tetrahedron, 47, 9503-9503 (1991)
Munchhoff, M.J. Meters, A.I.
The Journal of Organic Chemistry, 60, 7086-7086 (1995)
Andres, C.J. et al.
Tetrahedron Letters, 60, 3189-3189 (1995)
Brengel, G.P. Meyers, A.I.
The Journal of Organic Chemistry, 61, 3230-3230 (1996)
A Rapid and Efficient Approach to Chiral, Nonracemic Aza Sugars from Nonsugars. A Formal Synthesis of 1,4-Dideoxy-1,4-imino-D-lyxitol.
A. I. Meyers et al.
The Journal of organic chemistry, 61(8), 2586-2587 (1996-04-19)

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