✦ LIBER ✦
Asymmetric synthesis of α-aminophosphonic acids, I enantioselective synthesis of L-(1-aminoethyl)phosphonic acid by asymmetric catalytic hydrogenation ofN-[1-(dimethoxyphosphoryl)ethenyl]formamide
✍ Scribed by Schöllkopf, Ulrich ;Hoppe, Inga ;Thiele, Angelika
- Book ID
- 102364518
- Publisher
- John Wiley and Sons
- Year
- 1985
- Tongue
- English
- Weight
- 275 KB
- Volume
- 1985
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The synthesis of N‐[bis(dimethoxyphosphoryl)methyl]formamide (7) from aminomethylene‐bis(phosphonic acid) (6) is described. 7 reacts with aldehydes in a Wittig‐Horner reaction to give N‐[1‐(dimethoxyphosphoryl)‐1‐alkenyl]formamides 3. From the parent compound 3a L‐(1‐amino‐ethyl)phosphonic acid (1) is obtained with e.e. ca. 76% via asymmetric catalytic hydrogenation using a rhodium catalyst in the presence of (+)‐DIOP.