Improved and efficient synthesis of chiral N,P-Ligands via cyclic sulfamidates for asymmetric addition of butyllithium to benzaldehyde

• A robust and scaleable route to chiral 1-isopropylamino-2-(diphenylphosphino)ethanes is described via the ring-opening of chiral, cyclic sulfamidates with potassium diphenylphosphide (KPPh2). The novel protocol offers a robust access to gram quantities of chiral amino phosphinoethanes in high yields. The Li-amides of the chiral aminophosphines were evaluated as chiral ligands in the asymmetric addition of n-butyllithium (BuLi) to benzaldehyde, yielding 1-phenylpentanol up to 98% ee.

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Keyword

ENANTIOSELECTIVE ADDITION

ALKYLLITHIUM REAGENTS

ALLYLIC ALKYLATION

LITHIUM AMIDES

ALDEHYDES

LIGANDS

Publication and Content Type

ref (subject category)

art (subject category)