The structures of cyclic aminals from aldehydes and “roofed” mono-N-sulfonyl cis-diamines

ABSTRACT

Racemic Aldehydes were converted into aminals by using “roofed” mono-N-sulfonyl cis-diamines. Diastereomeric aminals could be separated by silica-gel TLC. The whole configuration of each aminal could be determined by NMR analyses. The chiral reagents were prepared from aminals of racemic reagents and a chiral aldehyde. The reverse may be also true. Epimerization of some aminal remains to be solved.

Abbreviations: RDA-Ms: N-(12-amino-9,10-dihydro-9,10-ethanoanthracen-11-yl)-methylsulfonamide; RDA-Ts: N-(12-amino-9,10-dihydro-9,10-ethanoanthracen-11-yl)-4-methylbenzenesulfonamide; RDA-1Nps: N-(12-amino-9,10-dihydro-9,10-ethanoanthracen-11-yl)-1-　naphthylsulfonamide; RDA-2Nps: N-(12-amino-9,10-dihydro-9,10-ethanoanthracen-11-yl)-2-naphthylsulfonamide

KEYWORDS:

• Aldehyde
• “roofed” mono-N-sulfonyl cis-diamine
• cyclic aminal
• absolute configuration

Acknowledgments

We are grateful to Mr. Yusuke Takata and Dr. Eri Fukushi of the GC-MS and NMR Laboratory, Faculty of Agriculture, Hokkaido University for their skill and assistance in analyzing the NMR and MS data. A scholarship to L.A.A from JASSO is gratefully acknowledged.

Author contributions

Y. F designed the research plan, L.A. A, S. F. and Y. F. performed the experiments and analyzed data, and Y.F. supervised the research. L.A.A wrote the manuscript with assistance from Y.F.

Disclosure statement

No potential conflict of interest was reported by the authors.

Supplementary material

Supplemental data for this article can be accessed here.

Additional information

Funding

L.A.A receives a scholarship from Japan Student Services Organization (JASSO).