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l ‐Menthol‐Assisted Synthesis of P‐Stereogenic Phosphinous Acid Amides and Phosphine‐Boranes
Author(s) -
Włodarczyk Adam,
Kozioł Anna E.,
Stankevič Marek
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800065
Subject(s) - chemistry , boranes , borane , organic chemistry , electrophile , stereocenter , diastereomer , medicinal chemistry , hydroboration , synthon , phosphine , menthol , stereochemistry , enantioselective synthesis , boron , catalysis
Diastereomerically pure phenylphosphonous acid‐borane l ‐menthyl ester N , N ‐diethylamide was obtained through the fractional crystallization of a diastereomeric mixture of compounds synthesized from PhPCl 2 , l ‐menthol, diethylamine, and BH 3 · THF. Treatment of racemic or diastereomerically pure phenylphosphonous acid‐borane derivatives with sodium in liquid ammonia followed by the addition of an electrophile led to the formation of phosphinous acid‐amides. Surprisingly, these compounds undergo preferential P–N bond cleavage under Birch reduction conditions.