Direct catalytic asymmetric Mannich-type reaction of hydroxyketone using a Et2Zn/linked-BINOL complex: Synthesis of either anti- or syn-β-amino alcohols

Journal of the American Chemical Society

Volumn 126, Issue 28, 2004, Pages 8777-8785

  Matsunaga, Shigeki ^a   Yoshida, Takamasa ^a   Morimoto, Hiroyuki ^a   Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; COMPLEXATION; COMPUTATIONAL METHODS; KETONES; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

CATALYST TURNOVER NUMBER (TON); DIRECT CATALYTIC ASYMMETRIC MANNICH-TYPE REACTIONS; HYDROXYKETONES;

CATALYSIS;

ALCOHOL DERIVATIVE; AMINOALCOHOL; IMINE; KETOL; NITROGEN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; MANNICH REACTION; REACTION ANALYSIS; SYNTHESIS;

AMINO ALCOHOLS; CATALYSIS; KETONES; MOLECULAR STRUCTURE; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 3242668608     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0482435     Document Type: Article

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55. The precise coordination mode of imines to Zn catalyst is unclear. [mines would possibly coordinate to Zn through either the oxygen atom of the protective group or the nitrogen atom of imines. Because the present Zn/linked-BINOL/ketone 2a complex is oligomeric with as much as seven zinc metals, flexible coordination of imines to the Zn/linked-BINOL/ketone 2a complex seems possible.
56. For detailed results of initial rate kinetics, see the Supporting Information.
57. Although mechanistic studies including X-ray crystallography, mass, and kinetic profiles suggested oligomeric active species (see ref 16a), a linear relationship between the ee of linked-BINOL and the ee of product was observed. The linear relationship would suggest that the formation of heterocomplex from (S,S)-1 and (R,R)-1 would be negligible. See the Supporting Information for the detailed results.
58. Both Dpp-imine 3 and Boc-imine 4 are known as highly electrophilic imines. On the basis of its stability on silica gel against hydrolysis (Dpp-imine, stable; Boc-imine, decomposed), we speculate Boc-imine 4 would be more electrophilic than Dpp-imine 3.
59. In the mechanistic studies of Michael reaction of 2a, we found that Zn-(S,S)-linked-BINOL catalyst recognized the absolute configuration of α-hydroxyketone unit well, and therefore the affinity of the Michael adduct to zinc catalyst was low. Thus, high catalyst TON was achieved in the Michael reaction of 2a and methyl vinyl ketone. See ref 17a.
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