Enantioselective brønsted acid catalyzed addition reactions of methyleneaminopyrrolidine to imines

Synlett

Volumn , Issue 17, 2005, Pages 2635-2638

  Dixon, Darren J ^a   Tillman, A Louise ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Asymmetric synthesis; Hydrazone; Hydrogen bond donor; Imines; Organocatalysis

Indexed keywords

1 METHYLENEAMINOPYRROLIDINE; 1 PHENYL 2(PYRROLIDIN 1 YLIMINO)ETHYLCARBAMIC ACID TERT BUTYLESTER; 2,2 PISPHENOL; 3,3' BIS (HYDROXYDIPHENYLMETHYL) [1,1'] BINAPHTHALENYL 2,2' DIOL; 3,3' BIS [BIS(2 CHLOROPHENYL)HYDROXYMETHYL] [1,1'] BINAPHTHALENYL 2,2' DIOL; 3,3' BIS [BIS(3 METHOXYPHENYL)HYDROXYMETHYL] [1,1'] BINAPHTHALENYL 2,2' DIOL; ALPHA AMINOHYDRAZONE; BENZOPHENONE DERIVATIVE; ESTER DERIVATIVE; HYDRAZONE DERIVATIVE; IMINE; N TERT BUTYLOXYCARBONYLIMINE; PHENOL DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGEN BOND;

EID: 27544501769     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917098     Document Type: Article

References (27)

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21. 10 Their formation is thought to occur via a [2+2], retro-[2+2] cycloaddition sequence (Scheme 3).
22. Catalysts 17a, 18a and 18b were kindly donated by Isabel Villaneuva Margalef.
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24. 3, with no observable deleterious effect on yield or ee.
25. All imine substrates were made using the procedure reported by Jacobsen: Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
26. Absolute stereochemistry of adduct 16 was determined by the synthesis of a matched compound from (S)-N-Boc-phenylglycine and comparing retention times on chiral stationary phase HPLC. The absolute stereochemistry of all other adducts was assigned by analogy.
27. 3): δ = 152.1, 140.4, 139.9, 134.2, 133.4, 132.5, 132.0, 131.7, 131.6, 131.1, 130.9, 129.9, 129.8, 128.9, 128.7, 127.9, 127.2, 126.9, 126.4, 124.6, 123.6, 117.7, 85.4. IR (film): 3497