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anti-Selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing beta-amino alcohols.
J Am Chem Soc. 2003 Apr 23; 125(16):4712-3.JA

Abstract

An anti-selective direct catalytic asymmetric Mannich-type reaction is described. The Et(2)Zn/(S,S)-linked-BINOL 1 = 4/1 complex promoted a Mannich-type reaction of 2-hydroxy-2'-methoxyacetophenone (2) and N-diphenylphosphinoyl imines 3. Using as little as 0.25-1 mol % of the catalyst, we obtained Mannich adducts 4 in excellent yield (up to 99%), diastereoselectivity (anti/syn = up to >98/2), and enantiomeric excess (up to >99.5%). The anti-selectivity in the present system is complementary to that observed using previously reported methods, providing a novel efficient method to synthesize anti-beta-amino alcohols in a highly enantioselective manner. Facile deprotection of the N-diphenylphosphinoyl group and commercial availability of both Et(2)Zn solution and (S,S)-linked-BINOL 1 also make the present catalysis practical.

Authors+Show Affiliations

Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

12696881

Citation

Matsunaga, Shigeki, et al. "Anti-Selective Direct Catalytic Asymmetric Mannich-type Reaction of Hydroxyketone Providing Beta-amino Alcohols." Journal of the American Chemical Society, vol. 125, no. 16, 2003, pp. 4712-3.
Matsunaga S, Kumagai N, Harada S, et al. Anti-Selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing beta-amino alcohols. J Am Chem Soc. 2003;125(16):4712-3.
Matsunaga, S., Kumagai, N., Harada, S., & Shibasaki, M. (2003). Anti-Selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing beta-amino alcohols. Journal of the American Chemical Society, 125(16), 4712-3.
Matsunaga S, et al. Anti-Selective Direct Catalytic Asymmetric Mannich-type Reaction of Hydroxyketone Providing Beta-amino Alcohols. J Am Chem Soc. 2003 Apr 23;125(16):4712-3. PubMed PMID: 12696881.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - anti-Selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing beta-amino alcohols. AU - Matsunaga,Shigeki, AU - Kumagai,Naoya, AU - Harada,Shinji, AU - Shibasaki,Masakatsu, PY - 2003/4/17/pubmed PY - 2003/6/17/medline PY - 2003/4/17/entrez SP - 4712 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 16 N2 - An anti-selective direct catalytic asymmetric Mannich-type reaction is described. The Et(2)Zn/(S,S)-linked-BINOL 1 = 4/1 complex promoted a Mannich-type reaction of 2-hydroxy-2'-methoxyacetophenone (2) and N-diphenylphosphinoyl imines 3. Using as little as 0.25-1 mol % of the catalyst, we obtained Mannich adducts 4 in excellent yield (up to 99%), diastereoselectivity (anti/syn = up to >98/2), and enantiomeric excess (up to >99.5%). The anti-selectivity in the present system is complementary to that observed using previously reported methods, providing a novel efficient method to synthesize anti-beta-amino alcohols in a highly enantioselective manner. Facile deprotection of the N-diphenylphosphinoyl group and commercial availability of both Et(2)Zn solution and (S,S)-linked-BINOL 1 also make the present catalysis practical. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12696881/anti_Selective_direct_catalytic_asymmetric_Mannich_type_reaction_of_hydroxyketone_providing_beta_amino_alcohols_ L2 - https://doi.org/10.1021/ja034787f DB - PRIME DP - Unbound Medicine ER -