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Digitale Medien

Synthesis and chiroptical properties of a novel C2-symmetric binaphthyl phosphortriamide (”chiral HMPA“) (1997)

Meyers, A. I. ; Nguyen, Thanh ; Stoianova, Diana ; [weitere]

New York, NY [u.a.] : Wiley-Blackwell

Chirality 9 (1997), S. 431-434

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Details

ISSN: 0899-0042

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: By use of an asymmetric Ullmann coupling involving chiral naphthalene oxazolines 1, the title compounds were prepared in good yields and with high diastereoselectivity. Hydrolysis of the binaphthyl oxazolines 2 led to the di-aldehydes 5, which were transformed into the azepine derivative, 6. The latter was treated with the appropriate phosphoryl halide to access the chiral HMPA systems 7 and 9. The CD spectra of the chiral azepine 6 and the chiral phosphoramides 7 and 9 were measured and showed a strong positive CD couplet near 225 nm, consistent with the P axial chirality (S configuration). Semi-empirical CNDO/S molecular orbital calculations of the CD spectrum of 6 satisfactorily reproduced the major features of the observed spectrum. Chirality 9:431-434, 1997. © 1997 Wiley-Liss, Inc.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

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Meyers, A. I. ; Price, D. A.

New York, NY [u.a.] : Wiley-Blackwell

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