The asymmetric synthesis of chiral cyclic α-hydroxy phosphonates and quaternary cyclic α-hydroxy phosphonates.
نویسندگان
چکیده
A highly practical, catalytic enantioselective cyclic phosphite addition to aldehydes and ketones was developed. The reaction rate of the asymmetric hydrophosphonylation was significantly enhanced by the addition of silver carbonate. Particularly, significant improvement has been achieved on the asymmetric hydrophosphonylation of unactivated ketones, giving quaternary α-hydroxy phosphonates with excellent enantioselectivity (up to 99% ee).
منابع مشابه
Asymmetric organocatalytic synthesis of quaternary α-hydroxy phosphonates: en route to α-aryl phosphaisoserines.
The dual activation of acyl phosphonates and formaldehyde tert-butyl hydrazone by a BINAM-derived bis-urea catalyst is the key to achieve high reactivities and enantioselectivities in the synthesis of densely functionalized quaternary α-hydroxy phosphonates. Subsequent high-yielding transformations in a 'one-pot' fashion provide direct access to valuable azoxy compounds and quaternary α-aryl-ph...
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An unusual dinuclear chiral iron complex has been synthesized and effectively utilized in the asymmetric hydrophosphorylation of aldehydes to synthesize optically active α-hydroxy phosphonates with excellent yield and good enantioselectivity.
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We report our results concerning the first squaramide-catalysed hydrophosphonylation of aldehydes. In all cases, the reactions proceeded smoothly and cleanly under mild reaction conditions rendering final α-hydroxy phosphonates in very good yields and high enantioselectivities. It is one of the few organocatalytic examples of this reaction using aldehydes. It is the first time that diphenylphos...
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 10 8 شماره
صفحات -
تاریخ انتشار 2012